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2-Hydroxytetrahydrofuran, with the CAS number 5371-52-8, is a colorless liquid compound that is valuable in the field of organic synthesis. It is known for its unique chemical properties that make it a versatile building block for creating a wide range of chemical compounds and materials.

5371-52-8

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5371-52-8 Usage

Uses

Used in Organic Synthesis:
2-Hydroxytetrahydrofuran is used as a key intermediate in the synthesis of various organic compounds. Its chemical structure allows it to be easily modified and incorporated into more complex molecules, making it a valuable asset in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Hydroxytetrahydrofuran is used as a building block for the development of new drugs. Its unique structure and reactivity enable the creation of novel drug candidates with potential therapeutic applications, contributing to the advancement of medical treatments.
Used in Agrochemical Industry:
2-Hydroxytetrahydrofuran is also utilized in the agrochemical industry for the synthesis of new pesticides and other crop protection agents. Its versatility in organic synthesis allows for the development of innovative compounds that can help improve crop yields and protect against various pests and diseases.
Used in Specialty Chemicals:
In the specialty chemicals sector, 2-Hydroxytetrahydrofuran is employed in the production of various high-value chemicals, such as fragrances, dyes, and additives. Its unique properties make it an ideal candidate for the development of new materials with specific applications in various industries, including cosmetics, textiles, and plastics.

Check Digit Verification of cas no

The CAS Registry Mumber 5371-52-8 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,3,7 and 1 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 5371-52:
(6*5)+(5*3)+(4*7)+(3*1)+(2*5)+(1*2)=88
88 % 10 = 8
So 5371-52-8 is a valid CAS Registry Number.

5371-52-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-hydroxytetrahydrofuran

1.2 Other means of identification

Product number -
Other names hydroxytetrahydrofuran

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5371-52-8 SDS

5371-52-8Synthetic route

Ph3 P

Ph3 P

N-ethylpropionamide
5129-72-6

N-ethylpropionamide

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
HRh(CO)(PPh3)3 In para-xylene93%
N-ethylpropionamide
5129-72-6

N-ethylpropionamide

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With triphenylphosphine; HRh(CO)(PPh3)3 In para-xylene93%
4-butanolide
96-48-0

4-butanolide

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With diisobutylaluminium hydride In toluene at -78℃; for 1h; Reduction;79%
With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; for 3h;64%
With diisobutylaluminium hydride In toluene at -78℃; for 3h;52%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With dihydrogen peroxide at 45℃; for 24h;76%
With hydrogenchloride at 0 - 20℃;67%
With hydrogenchloride; water at 0℃; for 0.5h;61%
1,4-butenediol
6117-80-2

1,4-butenediol

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

Conditions
ConditionsYield
With hydrogen; montmorillonite-diphenylphosphinepalladium(II) under 760 Torr; for 30h; Ambient temperature;A 72%
B n/a
tetrahydrofuran
109-99-9

tetrahydrofuran

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With C36H40Cu2N6O2(2+) In acetone at -70℃;62%
With tert.-butylhydroperoxide; copper(l) chloride
With 3,3-dimethyldioxirane In acetone at 25℃; Kinetics;96 % Chromat.
With [{Cu(II)(Me2NMePY2)}2(O2)](B(C6H5)4)2 In dichloromethane at -80℃; Product distribution; Kinetics; Further Variations:; Reagents; other substrates;
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane; water at 139.84℃; under 60006 Torr; for 4h;A 5%
B 52%
tetrahydrofuran
109-99-9

tetrahydrofuran

2-hydroperoxytetrahydrofuran
4676-82-8

2-hydroperoxytetrahydrofuran

acrylonitrile
107-13-1

acrylonitrile

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

2-(β-cyanoethyl)tetrahydrofuran
16237-62-0

2-(β-cyanoethyl)tetrahydrofuran

C

3-[2-(2-Cyano-ethyl)-tetrahydro-furan-2-yl]-propionitrile

3-[2-(2-Cyano-ethyl)-tetrahydro-furan-2-yl]-propionitrile

D

2-(Tetrahydro-furan-2-ylmethyl)-pentanedinitrile

2-(Tetrahydro-furan-2-ylmethyl)-pentanedinitrile

E

3-[5-(2-Cyano-ethyl)-tetrahydro-furan-2-yl]-propionitrile

3-[5-(2-Cyano-ethyl)-tetrahydro-furan-2-yl]-propionitrile

Conditions
ConditionsYield
at 130℃; for 4h; Product distribution; Mechanism; He-atmosphere, other temperatures, times and initiators;A n/a
B 49%
C n/a
D n/a
E n/a
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

3-Hydroxytetrahydrofuran
453-20-3

3-Hydroxytetrahydrofuran

C

tetrahydrofuran-2'-yl ether
71780-57-9

tetrahydrofuran-2'-yl ether

Conditions
ConditionsYield
With water; hydrogen In 1,4-dioxane at 139.84℃; under 60006 Torr; for 4h;A 18%
B 8%
C 46%
With water; hydrogen; pyrographite In 1,4-dioxane at 139.84℃; under 60006 Torr; for 4h;A 18%
B 8%
C 46%
tetrahydrofuran
109-99-9

tetrahydrofuran

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

Conditions
ConditionsYield
With cobalt(III) acetylacetonate; oxygen In ethyl acetate at 70℃; for 24h; Product distribution; various cyclic ethers;A 9%
B 30%
With tert.-butylhydroperoxide; water; copper(II) bis(trifluoromethanesulfonate) at 90℃; for 20h; Inert atmosphere;A 21%
B 7%
With dihydrogen peroxide In water at 66℃; for 4h; Temperature; Green chemistry;A 6.85%
B 16.65%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

Conditions
ConditionsYield
sulfuric acid for 0.333333h; Title compound not separated from byproducts;A 28%
B 15%
With hydrogenchloride In water for 0.0833333h; Title compound not separated from byproducts;
With hydrogenchloride; water In dichloromethane at 20℃; for 5h; Overall yield = 84 %; Overall yield = 29.6 g;
tetrahydrofuran
109-99-9

tetrahydrofuran

2-methylquinoline
91-63-4

2-methylquinoline

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

2,4-dimethylquinoline
1198-37-4

2,4-dimethylquinoline

C

2-methylquinoline N-oxide
1076-28-4

2-methylquinoline N-oxide

D

2‐methyl‐4‐(tetrahydrofuran‐2‐yl)quinoline
104293-35-8

2‐methyl‐4‐(tetrahydrofuran‐2‐yl)quinoline

Conditions
ConditionsYield
With 3,3-dimethyldioxirane; trifluoroacetic acid In acetone at 50℃; Further byproducts given;A n/a
B 3.2%
C 23%
D 2.8%
2-methylquinoline
91-63-4

2-methylquinoline

3,3-dimethyldioxirane
74087-85-7

3,3-dimethyldioxirane

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

2,4-dimethylquinoline
1198-37-4

2,4-dimethylquinoline

C

2-methylquinoline N-oxide
1076-28-4

2-methylquinoline N-oxide

D

2‐methyl‐4‐(tetrahydrofuran‐2‐yl)quinoline
104293-35-8

2‐methyl‐4‐(tetrahydrofuran‐2‐yl)quinoline

Conditions
ConditionsYield
With tetrahydrofuran; trifluoroacetic acid In acetone at 50℃; Further byproducts given;A n/a
B 3.2%
C 23%
D 2.8%
2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

tetrahydrofuran-2'-yl ether
71780-57-9

tetrahydrofuran-2'-yl ether

Conditions
ConditionsYield
With hydrogen In 1,4-dioxane; water at 139.84℃; under 60006 Torr; for 4h;A 13%
B 7%
tetrahydrofuran
109-99-9

tetrahydrofuran

sodium acetate
127-09-3

sodium acetate

benzene diazonium chloride
100-34-5

benzene diazonium chloride

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

4-hydroxybutyraldehyde
25714-71-0

4-hydroxybutyraldehyde

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

4-formyloxy-butyraldehyde
24350-41-2

4-formyloxy-butyraldehyde

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With potassium carbonate In methanol
tetrahydrofuran
109-99-9

tetrahydrofuran

carbon dioxide
124-38-9

carbon dioxide

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

succinic acid anhydride
108-30-5

succinic acid anhydride

D

formic acid
64-18-6

formic acid

Conditions
ConditionsYield
With (bis(1,2-diphenylphosphino)ethane)(2,5-norbornadiene)rhodium(I) tetrafluoroborate; oxygen at 25℃; under 2585.7 - 25857.4 Torr; for 192h; other temp.; aerobic oxidation of other ethers;
tetrahydrofuran
109-99-9

tetrahydrofuran

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

octahydro-2,2′-bifuran
1592-33-2

octahydro-2,2′-bifuran

C

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
zinc sulfide In water for 24h; Product distribution; Quantum yield; Irradiation;A 0.2 mmol
B 20.5 mmol
C 1.2 mmol
tetrahydrofuran
109-99-9

tetrahydrofuran

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

succinic acid anhydride
108-30-5

succinic acid anhydride

D

butanedial
638-37-9

butanedial

Conditions
ConditionsYield
With FeCl2*THF; oxygen under 772.6 Torr; for 0.5h; Product distribution; Ambient temperature; other methal complexes catalysts, other reagent (O2 + CO2) , also styrene;
tetrahydrofuran
109-99-9

tetrahydrofuran

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

4-butanolide
96-48-0

4-butanolide

C

succinic acid
110-15-6

succinic acid

Conditions
ConditionsYield
With Anodic oxidation In sulfuric acid at 35℃; Product distribution; Mechanism; The effect of various anode materials (bright Pt, Pb/PbO2, glassy carbon, graphite), current density, concentration of THF (1-6M), temperature (20-35-50 deg C), and pH (0-6).;
In sulfuric acid at 35℃; Anodic oxidation; anode: bright Pt, current density: 400 mA cm-2;
In sulfuric acid at 35℃; Anodic oxidation; anode: Pb/PbO2, current density: 10 mA cm-2;
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

C

1,4-butenediol
6117-80-2

1,4-butenediol

Conditions
ConditionsYield
With hydrogen; Montmorillonite-Ph2PPd(II) In tetrahydrofuran at 25℃; under 760 Torr; for 2h; Product distribution; other catalysts (5percent Pd-C, Lindlar catalyst), other solvents (ethyl acetate);
1,4-butenediol
6117-80-2

1,4-butenediol

A

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

B

Butane-1,4-diol
110-63-4

Butane-1,4-diol

Conditions
ConditionsYield
With hydrogen; Montmorillonite-Ph2PPd(II) In tetrahydrofuran at 25℃; under 760 Torr; for 2h; Product distribution; other catalysts (Lindlar catalyst); no solvent; at 50 deg C;
Propionic acid tetrahydro-furan-2-yl ester

Propionic acid tetrahydro-furan-2-yl ester

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Mechanism; Kinetics; Rate constant; other reagents (pH dependence), other solvent, temperature; activation parameters;
Propionic acid tetrahydro-pyran-2-yl ester
208852-01-1

Propionic acid tetrahydro-pyran-2-yl ester

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Mechanism; Kinetics; Rate constant; other reagents (pH dependence), other solvent, temperature; activation parameters;
tetrahydrofuran-2-yl pivalate

tetrahydrofuran-2-yl pivalate

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; other reagents (pH dependence);
3-Chloro-propionic acid tetrahydro-furan-2-yl ester

3-Chloro-propionic acid tetrahydro-furan-2-yl ester

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; other reagents (pH dependence);
2-Bromo-propionic acid tetrahydro-furan-2-yl ester

2-Bromo-propionic acid tetrahydro-furan-2-yl ester

2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

Conditions
ConditionsYield
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; other reagents (pH dependence);
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

tetrahydrofuran
109-99-9

tetrahydrofuran

Conditions
ConditionsYield
With phosphoric acid; 5%-palladium/activated carbon; hydrogen at 100℃; under 3750.38 - 13501.4 Torr; for 7h; Reagent/catalyst; Pressure; Temperature; Autoclave;100%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane
66323-99-7

trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane

1-phenyl-2-(tetrahydrofuran-2-yl)-propan-1-one

1-phenyl-2-(tetrahydrofuran-2-yl)-propan-1-one

Conditions
ConditionsYield
With indium(III) chloride at 20℃; for 0.5h;98%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

vinylmagnesium chloride
3536-96-7

vinylmagnesium chloride

1,4-dihydroxy-hex-5-ene
41324-11-2

1,4-dihydroxy-hex-5-ene

Conditions
ConditionsYield
In tetrahydrofuran 1.) 0 deg C to r.t., 15 min, 2.) r.t., 2 h;95%
In tetrahydrofuran53%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

isopropyl alcohol
67-63-0

isopropyl alcohol

2-isopropoxytetrahydrofuran
20191-91-7

2-isopropoxytetrahydrofuran

Conditions
ConditionsYield
With titanium(IV) tetrabutoxide; (R)-Mandelic Acid at 20℃; for 24h;95%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

1-styrenyloxytrimethylsilane
13735-81-4

1-styrenyloxytrimethylsilane

1-phenyl-2-(tetrahydrofuran-2-yl)ethan-1-one
59137-68-7

1-phenyl-2-(tetrahydrofuran-2-yl)ethan-1-one

Conditions
ConditionsYield
With indium(III) chloride at 20℃; for 0.5h;94%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

acetylacetone
123-54-6

acetylacetone

3-(tetrahydrofuran-2-yl)-2,4-pentanedione
122722-52-5

3-(tetrahydrofuran-2-yl)-2,4-pentanedione

Conditions
ConditionsYield
With indium(III) chloride at 20℃; for 40h;93%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

1-triphenylphosphoranylidene-2-propanone
1439-36-7

1-triphenylphosphoranylidene-2-propanone

(E)-7-hydroxyhept-3-en-2-one
757231-85-9

(E)-7-hydroxyhept-3-en-2-one

Conditions
ConditionsYield
In dichloromethane at 40℃; Wittig reaction;92%
In dichloromethane at 45℃; for 6h; Wittig Rearrangement;78%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2,3-dihydro-2H-furan
1191-99-7

2,3-dihydro-2H-furan

Conditions
ConditionsYield
With porcelain at 240℃; Product distribution; Further Variations:; Reagents; Temperatures; vapor-gas phase reaction;91%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

phenylmagnesium bromide
100-58-3

phenylmagnesium bromide

1-phenyl-butane-1,4-diol
4850-50-4

1-phenyl-butane-1,4-diol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h;90%
In tetrahydrofuran at 20℃; for 0.333333h;85%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

jaspine B
356043-02-2

jaspine B

3-[(2R,3aS,6S,6aS)-6-tetradecylhexahydrofuro[3,4-d]oxazol-2-yl]-1-propanol

3-[(2R,3aS,6S,6aS)-6-tetradecylhexahydrofuro[3,4-d]oxazol-2-yl]-1-propanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In methanol at 20℃; for 17h;89%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2-(2-nitro-vinyl)-phenol
3156-43-2

2-(2-nitro-vinyl)-phenol

A

(3aR,4S,9aS)-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

(3aR,4S,9aS)-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

B

4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 23℃; for 24h; Reagent/catalyst; Solvent; Concentration; Michael Addition; enantioselective reaction;A 89%
B n/a
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2-(2-nitro-vinyl)-phenol
3156-43-2

2-(2-nitro-vinyl)-phenol

(3aR,4S,9aS)-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

(3aR,4S,9aS)-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

Conditions
ConditionsYield
Stage #1: 2-hydroxytetrahydrofuran; 2-(2-nitro-vinyl)-phenol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 25℃; for 24h;
Stage #2: With hydrogenchloride In dichloromethane; water for 2h;
89%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2-thienyl lithium
2786-07-4

2-thienyl lithium

1-(2'-thienyl)-1,4-butanediol
75288-41-4

1-(2'-thienyl)-1,4-butanediol

Conditions
ConditionsYield
In tetrahydrofuran at 0 - 20℃; for 1.5h; Addition;88%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2,3-dimethyl-buta-1,3-diene
513-81-5

2,3-dimethyl-buta-1,3-diene

(4R,6S)-6,7-Dimethyl-oct-7-ene-1,4-diol

(4R,6S)-6,7-Dimethyl-oct-7-ene-1,4-diol

Conditions
ConditionsYield
With triethyl borane; bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane at 20℃; for 23h;88%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2-(2-nitrovinyl)-4-methoxyphenol
35467-98-2

2-(2-nitrovinyl)-4-methoxyphenol

(3aR,4S,9aS)-6-methoxy-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

(3aR,4S,9aS)-6-methoxy-4-(nitromethyl)-3,3a,4,9a-tetrahydro-2H-furo[2,3-b]chromene

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 23℃; for 125h; Michael Addition; enantioselective reaction;86%
Stage #1: 2-hydroxytetrahydrofuran; 2-(2-nitrovinyl)-4-methoxyphenol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 25℃; for 24h;
Stage #2: With hydrogenchloride In dichloromethane; water for 2h;
86%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

allyl-trimethyl-silane
762-72-1

allyl-trimethyl-silane

2-allyltetrahydro-2H-furan
52426-82-1

2-allyltetrahydro-2H-furan

Conditions
ConditionsYield
With indium(III) chloride; trimethylsilyl bromide In acetonitrile for 2h; Heating;85%
With rhenium(VII) oxide In dichloromethane at 20℃; for 4h; Inert atmosphere;33%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

2-phenylethanol
60-12-8

2-phenylethanol

(±)-2-phenethoxytetrahydrofuran
52767-51-8

(±)-2-phenethoxytetrahydrofuran

Conditions
ConditionsYield
With rhenium(VII) oxide In dichloromethane at 20℃; for 1h; Inert atmosphere;83.1%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

triphenylphosphoranylidene succinimide
18092-16-5, 28118-79-8

triphenylphosphoranylidene succinimide

A

3(Z)-(4-hydroxypentylidene)-2,5-pyrrolidinedione
99885-61-7

3(Z)-(4-hydroxypentylidene)-2,5-pyrrolidinedione

B

3(E)-(4-hydroxypentylidene)-2,5-pyrrolidinedione
92013-82-6

3(E)-(4-hydroxypentylidene)-2,5-pyrrolidinedione

Conditions
ConditionsYield
In acetic acid Ambient temperature;A 6%
B 83%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

isoprene
78-79-5

isoprene

(4R,6S)-6-Methyl-oct-7-ene-1,4-diol

(4R,6S)-6-Methyl-oct-7-ene-1,4-diol

Conditions
ConditionsYield
With triethyl borane; bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane at 20℃; for 22h;83%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

1,1,1,3,3,3-hexamethyl-disilazane
999-97-3

1,1,1,3,3,3-hexamethyl-disilazane

2-(trimethylsiloxy)furan
65769-92-8

2-(trimethylsiloxy)furan

Conditions
ConditionsYield
With sulfuric acid In dichloromethane at 20℃; for 10h;82%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

(carbethoxyethylidene)triphenylphosphorane
21382-82-1

(carbethoxyethylidene)triphenylphosphorane

(E)-6-hydroxy-2-methyl-hex-2-enoic acid ethyl ester
70562-19-5

(E)-6-hydroxy-2-methyl-hex-2-enoic acid ethyl ester

Conditions
ConditionsYield
In dichloromethane at 20℃; for 16h;82%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

vinyl magnesium bromide
1826-67-1

vinyl magnesium bromide

1,4-dihydroxy-hex-5-ene
41324-11-2

1,4-dihydroxy-hex-5-ene

Conditions
ConditionsYield
In tetrahydrofuran for 14h; Ambient temperature;80%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

3-Pyrroline
109-96-6

3-Pyrroline

hydroxymethyl dihydropyrrolizine
83821-03-8

hydroxymethyl dihydropyrrolizine

Conditions
ConditionsYield
With benzoic acid In toluene at 110℃; for 24h; Inert atmosphere;80%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

diethoxyphosphoryl-acetic acid ethyl ester
867-13-0

diethoxyphosphoryl-acetic acid ethyl ester

(E)-6-hydroxy-hex-2-enoic acid ethyl ester
13038-15-8

(E)-6-hydroxy-hex-2-enoic acid ethyl ester

Conditions
ConditionsYield
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride In acetonitrile at 23℃; for 0.25h; Inert atmosphere;
Stage #2: 2-hydroxytetrahydrofuran In acetonitrile at 0 - 23℃; for 0.5h; Inert atmosphere;
80%
In toluene for 18h; Inert atmosphere; Reflux; optical yield given as %de; diastereoselective reaction;74%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

[1,4]naphthoquinone
130-15-4

[1,4]naphthoquinone

(6bR,9aS)-6b,7,8,9a-tetrahydrofuro[2,3-b]naphtho[2,1-d]furan-5-ol

(6bR,9aS)-6b,7,8,9a-tetrahydrofuro[2,3-b]naphtho[2,1-d]furan-5-ol

Conditions
ConditionsYield
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; acetic acid In ethanol; dimethyl sulfoxide at -40℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere; enantioselective reaction;79%
2-hydroxytetrahydrofuran
5371-52-8

2-hydroxytetrahydrofuran

hex-3-yne
928-49-4

hex-3-yne

dimethyl zinc(II)
544-97-8

dimethyl zinc(II)

4-methoxy-aniline
104-94-9

4-methoxy-aniline

buta-1,3-diene
106-99-0

buta-1,3-diene

(6E,10E,13E)-4-(4-methoxyphenylamino)-13-ethyl-14-methylhexadeca-6,10,13-trien-1-ol
1173177-81-5

(6E,10E,13E)-4-(4-methoxyphenylamino)-13-ethyl-14-methylhexadeca-6,10,13-trien-1-ol

Conditions
ConditionsYield
Stage #1: 2-hydroxytetrahydrofuran; 4-methoxy-aniline In tetrahydrofuran at 20℃; Inert atmosphere;
Stage #2: hex-3-yne; dimethyl zinc(II); buta-1,3-diene With bis(acetylacetonate)nickel(II); triphenylphosphine In tetrahydrofuran; hexane at 20℃; for 6h; Inert atmosphere;
78%

5371-52-8Relevant academic research and scientific papers

Dioxygen activation by siloxide complexes of chromium(II) and chromium(IV)

Schax, Fabian,Bill, Eckhard,Herwig, Christian,Limberg, Christian

, p. 12741 - 12745 (2014)

The reaction of a tripodal trisilanol with n-butyllithium and CrCl2 results in a dinuclear CrII complex (1), which is capable of cleaving O2 to yield in a unique complex (2) with an asymmetric diamond core composed of two CrIV=O units. Magnetic susceptibility data reveal significant exchange coupling of CrII (S=2) in 1 and large zero-field splitting for CrIV (S=1) in 2 owing to strong spin-orbit coupling of the ground state. The CrIV=O compound can also be generated using PhIO, and evidence was gathered that although it is the stable product isolated after excessive O2 treatment, it further activates O2 to yield an intermediate species that oxidizes THF or Me-THF. By extensive 18O labeling studies we were able to show, that in the course of this process 18O2 exchanges its label with siloxide O atoms of the ligand via terminal oxido ligands.

Oxidation of tetrahydrofuran to butyrolactone catalyzed by iron-containing clay

Ausavasukhi, Artit,Sooknoi, Tawan

, p. 435 - 441 (2015)

Thermally treated iron-containing clay was used as a greener oxidation catalyst for the conversion of tetrahydrofuran (THF) to butyrolactone (BTL). Mild liquid phase reactions were tested at 50-66 °C using hydrogen peroxide (H2O2) as an oxidizing agent. XRD, TGA, ESR, DR-UV, and FTIR revealed the dislodged iron oxide species formed by treating at ≥500 °C. Formation of active oxidizing species on the surface occurs on contact the dislodged Fe(III) oxide with H2O2. Such active species can promote the oxidation of THF, giving high yield and selectivity of BTL, whereas the iron-containing clay treated at lower temperatures (2O2/THF ratio of 1.0 is sufficient for the production of BTL. Deactivation can be observed presumably due to deposition of the products despite slight leaching of the active iron species.

Synthesis of functionalized bicyclic imines via intramolecular azide-alkene 1,3-dipolar cycloaddition/intramolecular stork alkylation cascade reaction

De Miguel, Irene,Velado, Marina,Herradon, Bernardo,Mann, Enrique

, p. 1237 - 1242 (2013)

A cascade intramolecular azide-alkene 1,3-dipolar cycloaddition/Stork alkylation reaction has been developed for the synthesis of functionalized cyclic imines with a pyrroline and piperideine structures, employing readily available ω-azidodienes. Copyright

Synthetic studies of ingenol: Synthesis of in,out- tricyclo[7.4.1.01,5]tetradecan-14-one

Kigoshi, Hideo,Suzuki, Yuto,Aoki, Kenta,Uemura, Daisuke

, p. 3927 - 3930 (2000)

in,out-Tricyclo[7.4.1.01,5]tetradecan-14-one was synthesized from γ- butyrolactone in 12 steps using ring-closing olefin metathesis as the key step. (C) 2000 Elsevier Science Ltd.

Genotoxicity screening for N-nitroso compounds. Electrochemical and electrochemiluminescent detection of human enzyme-generated DNA damage from N-nitrosopyrrolidine

Krishnan, Sadagopan,Hvastkovs, Eli G.,Bajrami, Besnik,Jansson, Ingela,Schenkman, John B.,Rusling, James F.

, p. 1713 - 1715 (2007)

We report for the first time voltammetric/electrochemiluminescent sensors applied to predict genotoxicity of N-nitroso compounds bioactivated by human cytochrome P450 enzymes. The Royal Society of Chemistry.

Formal synthesis of optically active ingenol via ring-closing olefin metathesis

Watanabe, Kazushi,Suzuki, Yuto,Aoki, Kenta,Sakakura, Akira,Suenaga, Kiyotake,Kigoshi, Hideo

, p. 7802 - 7808 (2004)

The construction of strained carbon skeletons by ring-closing olefin metathesis (RCM) was investigated. With well-designed diene 4, RCM was found to be applicable to the formation of a highly strained inside-outside bicyclo[4.4.1]undecane skeleton of ingenol, a bioactive diterpenoid, and formal total synthesis of optically active ingenol (1) was achieved. The key features of this synthesis are construction of an A-ring by spirocyclization of the ketone with an allylic chloride unit, 26, and ring closure of a B-ring by olefin metathesis. Starting from Funk's keto ester 6, the key intermediate aldehyde 9 in Winkler's total synthesis was synthesized in eight steps in 12.5% overall yield. This strategy of direct cyclization of a strained inside-outside skeleton provided the first easy access to optically active ingenol.

Free-radical approaches to stemoamide and analogues

Bogliotti, Nicolas,Dalko, Peter I.,Cossy, Janine

, p. 9528 - 9531 (2006)

(Chemical Equation Presented) Two approaches allowing access to the tricyclic stemona backbone are presented. Both approaches rely on a free-radical cyclization reaction as the key step. In the formal synthesis of (±)-stemoamide, the construction of the A ring of the natural product was achieved via a 5-exo-trig radical cyclization with atom transfer. The two diastereoisomers issuing from this cyclization showed different reactivity while forming the seven-membered ring of the final product. In the second part of this study, a 1-exo-trig free radical cyclization was realized allowing access to the (±)-9,10-bis-epi-stemoamide. This reaction was highly stereoselective and allowed the control of three of the four contiguous stereocenters present in the molecule.

Catalytic behaviour of the Cu(I)/L/TEMPO system for aerobic oxidation of alcohols - a kinetic and predictive model

Abu-Radaha, Batool,Al-Hunaiti, Afnan,Repo, Timo,Wraith, Darren

, p. 7864 - 7871 (2022/04/09)

Here, we disclose a new copper(i)-Schiff base complex series for selective oxidation of primary alcohols to aldehydes under benign conditions. The catalytic protocol involves 2,2,6,6-tetramethylpiperidine-N-oxyl (TEMPO), N-methylimidazole (NMI), ambient air, acetonitrile, and room temperature. This system provides a straightforward and rapid pathway to a series of Schiff bases, particularly, the copper(i) complexes bearing the substituted (furan-2-yl)imine bases N-(4-fluorophenyl)-1-(furan-2-yl)methanimine (L2) and N-(2-fluoro-4-nitrophenyl)-1-(furan-2-yl)methanimine (L4) have shown excellent yields. Both benzylic and aliphatic alcohols were converted to aldehydes selectively with 99% yield (in 1-2 h) and 96% yield (in 16 h). The mechanistic studies via kinetic analysis of all components demonstrate that the ligand type plays a key role in reaction rate. The basicity of the ligand increases the electron density of the metal center, which leads to higher oxidation reactivity. The Hammett plot shows that the key step does not involve H-abstraction. Additionally, a generalized additive model (GAM, including random effect) showed that it was possible to correlate reaction composition with catalytic activity, ligand structure, and substrate behavior. This can be developed in the form of a predictive model bearing in mind numerous reactions to be performed or in order to produce a massive data-set of this type of oxidation reaction. The predictive model will act as a useful tool towards understanding the key steps in catalytic oxidation through dimensional optimization while reducing the screening of statistically poor active catalysis.

Dual C(sp3)-H Functionalization of Cyclic Ethers via Singlet Oxygen-Mediated Ring Opening and Ring Closing

Yuan, Xu,Yu, Xianglin,He, Kun,Zhang, Ruihan,Xiao, Weilie,Lin, Jun,Zhan, Zhajun,Cheng, Xiaohong,Shao, Zhihui,Jin, Yi

supporting information, p. 8267 - 8272 (2021/10/25)

A metal-free dual C(sp3)-H bond functionalization of saturated cyclic ethers via photooxidative singlet oxygen-mediated ring opening and ring closing has been developed, providing a method for generating hydrobenzofurans/pyrans/dioxins. Mechanistic studies have confirmed that ring-opening intermediates were effectively generated by singlet oxygen-mediated C(sp3)-H activation and efficiently reacted with aldehydes and activated methylene compounds to form a wide array of products with high diastereoselectivities (up to >95:5 dr). This study is a rare example of α,β-dual C(sp3)-H bond functionalization of ethers.

Visible light-induced Minisci reaction through photoexcitation of surface Ti-peroxo species

Naniwa, Shimpei,Yamamoto, Akira,Yoshida, Hisao

, p. 3376 - 3384 (2021/06/06)

Photocatalytic Minisci-type functionalization of pyridine with tetrahydrofuran (THF) proceeded using hydrogen peroxide (H2O2) and a TiO2photocatalyst under acidic conditions. Under UV light (λ= 360 nm), the reaction selectivity based on pyridine (Spy) was >99% while the selectivity based on THF (STHF) was low such as 19%. In contrast, under visible light (λ= 400 or 420 nm)Spywas similarly high (>99%) andSTHFwas two times higher than that under UV light. A surface peroxo complex formed upon contact of hydrogen peroxide with the TiO2surface can be selectively photoexcited by visible light to inject the photoexcited electron to the conduction band of TiO2. The electron can reduce H2O2to a reactive oxygen species (ROS) and promote selectively the Minisci-type cross-coupling reaction between pyridinium ions and THF. A reaction test with a hole scavenger (methanol) evidenced that the hole oxidation of H2O2under UV light is responsible for the lower selectivity, in other words, the higher selectivity under visible light would be due to suppression of the hole oxidation of H2O2. These results demonstrate a novel way to improve the selectivity of the photocatalytic cross-coupling reaction by using H2O2as an oxidant with the photoexcitation of surface Ti-peroxo species on TiO2

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