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5371-52-8 Usage

Chemical Properties

Colourless Liquid

Uses

2-Hydroxytetrahydrofuran (cas# 5371-52-8) is a compound useful in organic synthesis.

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 articles and documents

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.

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

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.

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.

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.

Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents

Llopis, Natalia,Gisbert, Patricia,Baeza, Alejandro

supporting information, p. 3245 - 3249 (2021/06/08)

The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2-ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger-scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. (Figure presented.).

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