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δ-Valerolactone
Cas No: 542-28-9
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delta-Valerolactone CAS 542-28-9 IN Stock Tetrahydro-2H-2-pyranone 542-28-9
Cas No: 542-28-9
USD $ 3.5-5.0 / Kiloliter 5 Kiloliter 3000 Metric Ton/Month Chemwill Asia Co., Ltd. Contact Supplier
High quality Delta Valerolactone supplier in China
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delta-Valerolactone
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delta-Valerolactone Manufacturer/High quality/Best price/In stock
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USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
Delta-Valerolactone CAS: 542-28-9
Cas No: 542-28-9
USD $ 1.0-1.0 / Kilogram 1 Kilogram 1000 Metric Ton/Year Henan Sinotech Import&Export Corporation Contact Supplier
cheap delta-Valerolactone bulk supply reliable quality 542-28-9
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USD $ 1.0-1.0 / Kilogram 1 Kilogram 100 Kilogram/Month Shenzhen Tianyuan Pharmaceutical Technology Co., Ltd Contact Supplier
TIANFU-CHEM CAS:542-28-9 delta-Valerolactone
Cas No: 542-28-9
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"HighqualityDelta-Valerolactone(DVL),CASNO:542-28-9 "
Cas No: 542-28-9
USD $ 1.0-2.0 / Metric Ton 1 Metric Ton 2 Metric Ton/Day Hubei Jusheng Technology Co., Ltd., Contact Supplier
Pharmaceutical Grade CAS 542-28-9 with competitive price
Cas No: 542-28-9
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542-28-9 Usage

Purification Methods

Purify the -lactone by repeated fractional distillation. IR: max 1750 (in CS2), 1732 (in CHCl3),1748 (in CCl4) and 1733 (in MeOH) cm-1 [Huisgen & Ott Tetrahedron 6 253 1959, Linstead & Rydon J Chem Soc 580 1933, Jones et al. Can J Chem 37 2007 1959]. [Beilstein 17 H 235, 17 II 287, 17 III/IV 4169,17/9 V 17.]

Definition

ChEBI: The simplest member of the class of delta-lactone that is tetrahydro-2H-pyran substituted by an oxo group at position 2.

Chemical Properties

clear colorless to pale yellow liquid
InChI:InChI=1/C5H8O2/c6-5-3-1-2-4-7-5/h1-4H2

542-28-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Aldrich (389579)  δ-Valerolactone  technical grade 542-28-9 389579-100ML 1,732.77CNY Detail
Aldrich (389579)  δ-Valerolactone  technical grade 542-28-9 389579-25ML 546.39CNY Detail
Alfa Aesar (L04794)  delta-Valerolactone, 98%, may contain polymer    542-28-9 500g 4020.0CNY Detail
Alfa Aesar (L04794)  delta-Valerolactone, 98%, may contain polymer    542-28-9 100g 1052.0CNY Detail
Alfa Aesar (L04794)  delta-Valerolactone, 98%, may contain polymer    542-28-9 25g 386.0CNY Detail
TCI America (V0039)  δ-Valerolactone  >98.0%(GC) 542-28-9 500g 2,920.00CNY Detail
TCI America (V0039)  δ-Valerolactone  >98.0%(GC) 542-28-9 100g 1,120.00CNY Detail
TCI America (V0039)  δ-Valerolactone  >98.0%(GC) 542-28-9 25g 380.00CNY Detail

542-28-9SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 5-valerolactone

1.2 Other means of identification

Product number -
Other names δ-Valerolactone

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:542-28-9 SDS

542-28-9Synthetic route

5,6-dihydro-pyran-2-one
3393-45-1

5,6-dihydro-pyran-2-one

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With hydrogen; palladium(II) complex of ferrocenylamine sulfide (1) In acetone under 4137.2 Torr; for 10h;100%
1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydrogencarbonate; potassium bromide In dichloromethane at 0℃; for 0.5h; chemoselective reaction;99%
With sodium bromite In water; acetic acid for 10h; Ambient temperature;98%
With 4-hydroxy-TEMPO benzoate; sodium bromide In dichloromethane; water NaHCO3-buffered at pH 8.6; electrolysis;97%
cyclopentanone
120-92-3

cyclopentanone

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With Octanoic acid; dihydrogen peroxide In water at 50℃; for 5h; Baeyer-Villiger oxidation; Ionic liquid; Enzymatic reaction;99%
With dihydrogen peroxide; lithium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate In water; 1,2-dichloro-ethane at 70℃; for 2h; Time; Temperature; Reagent/catalyst;99%
With dihydrogen peroxide; polystyrene-bound phenylselenic acid In dichloromethane for 72h; Ambient temperature;98%
valeric acid
13392-69-3

valeric acid

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With molecualar sevies 4A; tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene at 120℃; for 10h;98%
tetrachlorobis(tetrahydrofuran)hafnium(IV) In toluene for 10h; Heating;96%
With cis-nitrous acid at 25℃; Rate constant;
Equilibrium constant; Rate constant;
propyl 5-hydroxyvalerate

propyl 5-hydroxyvalerate

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 732 sulfonic acid type cation exchange resin at 150℃; for 2h; Time;96.31%
ethyl 2-hydroxyethylpropionate
13107-53-4

ethyl 2-hydroxyethylpropionate

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 732 sulfonic acid type cation exchange resin at 130℃; for 1.5h;96.05%
5-chloro-valeric acid
1119-46-6

5-chloro-valeric acid

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With sodium hydroxide for 0.166667h; Heating;96%
With triethylamine at 50℃; under 3750300 Torr; for 3h;90%
With cyclohexene In gas at 349.5℃; for 0.1h; Rate constant; stoichometry;44.3%
5-bromopentanoic acid
2067-33-6

5-bromopentanoic acid

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With potassium fluoride; tetra(n-butyl)ammonium hydrogensulfate In tetrahydrofuran at 20℃; for 5h;96%
With Amberlyst A26 (hydrogen carbonate form) 1.) aq. MeOH, 20 deg C, 18 h, 2.) THF, reflux, 18 h; Yield given. Multistep reaction;
With potassium carbonate In water; dimethyl sulfoxide at 50℃; Rate constant;
With 2,3,3-trimethylbenzo[e]indole; potassium iodide In acetonitrile at 80 - 85℃; for 96h;
methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 732 sulfonic acid type cation exchange resin at 100℃; for 1h; Time;95.08%
porcine pancreatic lipase In diethyl ether at 26℃;
Butane-1,4-diol
110-63-4

Butane-1,4-diol

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With trichloromelamine In dichloromethane for 12h; Mechanism; Ambient temperature;95%
5-hydroxypentylamine
2508-29-4

5-hydroxypentylamine

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With hydrogenchloride; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor In water for 15h; pH=5.5; Enzymatic reaction; chemoselective reaction;95%
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With potassium permanganate; iron(III) chloride In acetone at -78 - 20℃; for 16h;92%
With zinc(II) permanganate; silica gel In dichloromethane at 20℃; for 0.17h;69%
Stage #1: TETRAHYDROPYRANE With [bis(acetoxy)iodo]benzene In nitromethane at 0℃;
Stage #2: With tert.-butylhydroperoxide In decane; nitromethane at 0 - 25℃; for 12h;
68%
Cyclopentanol
96-41-3

Cyclopentanol

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 20h;92%
With dihydrogen peroxide In water at 20℃; for 7h; Baeyer-Villiger-type reaction;92%
With water; fluorine In acetonitrile
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane at 60℃; for 24h; Product distribution; Mechanism; other solvent;
5-hydroxypentanal
4221-03-8

5-hydroxypentanal

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With N-iodo-succinimide; silver(I) acetate In benzene for 3h; Heating;90%
With dihydrogen peroxide; acetic acid
With manganese(IV) oxide; chloroform
With cobalt(II) acetate at 80 - 90℃; beim Beh. mit Luft;
trimethylsilyl 5-iodopentanoate

trimethylsilyl 5-iodopentanoate

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h;90%
acetic acid
64-19-7

acetic acid

cyclopentanone
120-92-3

cyclopentanone

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

5-acetoxypentanoic acid
26976-70-5

5-acetoxypentanoic acid

Conditions
ConditionsYield
With peracetic acid 1.) 50-60 deg C, 6 h; 2.) reflux, 29 h;A n/a
B 85.5%
With peracetic acid 1.) 50-60 deg C, 6 h; 2.) reflux, 29 h; Yields of byproduct given;A n/a
B 85.5%
(CO)5MnCO(CH2)4OSi(CH3)3
77023-79-1

(CO)5MnCO(CH2)4OSi(CH3)3

tris(diethylamino)sulfonium difluorotrimethylsiliconate
59201-86-4

tris(diethylamino)sulfonium difluorotrimethylsiliconate

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

(CO)5Mn(1-)*{(CH3CH2)2N}3S(1+)=(CO)5Mn{(CH3CH2)2N}3S
89020-18-8

(CO)5Mn(1-)*{(CH3CH2)2N}3S(1+)=(CO)5Mn{(CH3CH2)2N}3S

Conditions
ConditionsYield
In tetrahydrofuran flask charged with ((CH3CH2)2N)3SSi(CH3)3F2, NMR standard and THF, complex in THF added dropwise for 0.5 h with stirring, stirred for 2 h; not isolated, detected by IR;A 85%
B n/a
<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, S*)
73819-79-1, 73819-80-4

<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, S*)

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

5,6-dihydro-2H-pyran-3(4H)-one
23462-75-1

5,6-dihydro-2H-pyran-3(4H)-one

<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, R*)
73819-79-1, 73819-80-4

<α-tetrahydropyrannyloxy>-2 tetrahydropyrone-3 (S*, R*)

Conditions
ConditionsYield
With further temp. In benzene at 80℃; for 1.5h; Product distribution; Irradiation;A 82%
B 16%
C 5%
ethyl valerolactonium tetrafluoroborate

ethyl valerolactonium tetrafluoroborate

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

ethyl 5-iodopentanoate
41302-32-3

ethyl 5-iodopentanoate

Conditions
ConditionsYield
With sodium iodide In dichloromethane; acetonitrileA 18%
B 82%
tetrahydrofuran-2-carbaldehyde
7681-84-7

tetrahydrofuran-2-carbaldehyde

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis[(2,6-diisopropyl)phenyl]imidazolinium chloride In dichloromethane at 20℃; for 5h; Inert atmosphere;82%
tetrahydropyran-2-yl hydroperoxide
4676-84-0

tetrahydropyran-2-yl hydroperoxide

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With tert-butylhypochlorite In acetonitrile at 20℃; for 0.166667h;78%
glutaric anhydride,
108-55-4

glutaric anhydride,

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran for 0.25h;77%
With ethanol; sodium
valeric acid
109-52-4

valeric acid

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

5-methyl-dihydro-furan-2-one
108-29-2

5-methyl-dihydro-furan-2-one

Conditions
ConditionsYield
With sodium persulfate In water at 85 - 90℃; for 5h;A 9%
B 77%
C6H11O2(1+)*BF4(1-)

C6H11O2(1+)*BF4(1-)

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

methyl 5-iodopentanoate
14273-88-2

methyl 5-iodopentanoate

Conditions
ConditionsYield
With sodium iodide In dichloromethane; acetonitrileA 29%
B 71%
1,4-Diiodobutane
628-21-7

1,4-Diiodobutane

Mo(CO)6

Mo(CO)6

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With potassium fluoride; 18-crown-6 ether; water In tetrahydrofuran for 20h; Heating;70%
TETRAHYDROPYRANE
142-68-7

TETRAHYDROPYRANE

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

Conditions
ConditionsYield
With sodium bromate; potassium hydrogensulfate In water at 25 - 30℃; for 20h; Oxidation;A 69%
B 16%
With 2,6-dichloropyridine N-oxide; dichloro(5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato)ruthenium(IV) In 1,2-dichloro-ethane at 40℃; for 20h; Reagent/catalyst; Inert atmosphere;A 56%
B 16%
cyclohexanol
108-93-0

cyclohexanol

A

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

B

Adipic acid
124-04-9

Adipic acid

C

monocyclohexyl adipate
54812-72-5

monocyclohexyl adipate

D

cyclohexanone
108-94-1

cyclohexanone

Conditions
ConditionsYield
With oxygen at 120℃; for 4.33333h; Further byproducts given;A 2.7%
B 12.4%
C 8.9%
D 65%
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Conditions
ConditionsYield
With hydrogen In methanol at 375℃; for 5h; Reagent/catalyst; Time; Solvent;65%
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C
2: [bis({2‐[bis(propan‐2‐yl)phosphanyl]ethyl})amine](borohydride)(carbonyl)(hydride)iron(II); potassium carbonate / toluene / 5 h / 150 °C / Inert atmosphere; Green chemistry
View Scheme
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

5-hydroxypentanoic acid sodium salt
37435-69-1

5-hydroxypentanoic acid sodium salt

Conditions
ConditionsYield
With water; sodium hydroxide at 20℃; Inert atmosphere;100%
With sodium hydroxide In ethanol at 20 - 80℃; for 2.5h;100%
With sodium hydroxide at 20℃; for 24h;83%
pyrrolidine
123-75-1

pyrrolidine

3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one
73200-35-8

5-hydroxy-1-(pyrrolidin-1-yl)pentan-1-one

Conditions
ConditionsYield
With triethylamine Inert atmosphere; Reflux;100%
In benzene82%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

methanol
67-56-1

methanol

methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

Conditions
ConditionsYield
With Dowex 50W-X8 resin at 20℃; Inert atmosphere; Reflux;100%
With sulfuric acid for 5h; Heating;99%
With H+ Dowex resin Heating;99%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

1-amino-2-propene
107-11-9

1-amino-2-propene

N-allyl-5-hydroxypentanamide
133055-24-0

N-allyl-5-hydroxypentanamide

Conditions
ConditionsYield
100%
In ethanol for 15h; Heating;63%
With bis(trifluoromethane)sulfonimide lithium In chloroform at 85℃; for 40h;5%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

formic acid ethyl ester
109-94-4

formic acid ethyl ester

Sodium; [2-oxo-dihydro-pyran-(3Z)-ylidene]-methanolate

Sodium; [2-oxo-dihydro-pyran-(3Z)-ylidene]-methanolate

Conditions
ConditionsYield
With sodium hydride100%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

1 ,5-pentanediol
111-29-5

1 ,5-pentanediol

Conditions
ConditionsYield
With trimethoxysilane; lithium methanolate In tetrahydrofuran for 0.5h; Ambient temperature;100%
With hydrogen In 1,2-dimethoxyethane at 80℃; under 60006 Torr; for 2h; Reagent/catalyst;87.7%
With sodium tetrahydroborate; C36H30F6N10Ni4O10(2+)*2C2F3O2(1-); zinc(II) chloride In tetrahydrofuran at 45℃; for 12h;79%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

(E)-benzyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate

(E)-benzyl 4,4,4-trifluoro-3-(trifluoromethyl)but-2-enoate

(3S*,2'S*)-Benzyl 3-pentan-5'-olid-2'-yl-3-(trifluoromethyl)propionate

(3S*,2'S*)-Benzyl 3-pentan-5'-olid-2'-yl-3-(trifluoromethyl)propionate

Conditions
ConditionsYield
With lithium diisopropyl amide In tetrahydrofuran; hexane 1.) -78 deg C, 30 min, 2.) -78 deg C;100%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

O-benzylhydoxylamine hydrochloride
2687-43-6

O-benzylhydoxylamine hydrochloride

N-(benzyloxy)-5-hydroxypentanamide

N-(benzyloxy)-5-hydroxypentanamide

Conditions
ConditionsYield
With trimethylaluminum In tetrahydrofuran; toluene100%
Stage #1: O-benzylhydoxylamine hydrochloride With trimethylaluminum In tetrahydrofuran; toluene at 0 - 20℃; for 0.833333h;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran; toluene at 0℃; for 1.5h;
50%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

methyl 5-hydroxypentanoate
14273-92-8

methyl 5-hydroxypentanoate

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 1h; Inert atmosphere; Large scale;100%
Stage #1: 3,4,5,6-tetrahydro-2H-pyran-2-one With sulfuric acid In methanol for 12h; Reflux;
Stage #2: With sodium hydrogencarbonate In methanol for 0.166667h; stereoselective reaction;
99%
With sulfuric acid In methanol for 12h; Reflux;94%
With sulfuric acid In methanol for 21h; Inert atmosphere; Reflux;85%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-aminoindane hydrochloride
2338-18-3

2-aminoindane hydrochloride

N-(indan-2-yl)-5-hydroxypentanamide
1148156-44-8

N-(indan-2-yl)-5-hydroxypentanamide

Conditions
ConditionsYield
With aluminum (III) chloride; triethylamine In 1,2-dichloro-ethane at 20℃; for 1h;100%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

phenylacetylene
536-74-3

phenylacetylene

5-oxo-5-(2-phenylethynyl)-1-pentanol
67654-84-6

5-oxo-5-(2-phenylethynyl)-1-pentanol

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h;
Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.166667h;
Stage #3: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78 - 20℃; for 1h;
99%
(i) nBuLi, hexane, THF, (ii) /BRN= 106436/; Multistep reaction;
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

1,3-Benzothiazole
95-16-9

1,3-Benzothiazole

1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one
85450-44-8

1-(benzo[d]thiazol-2-yl)-5-hydroxypentan-1-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; hexane -78 deg C, 1 h; to RT, 30 min;99%
Stage #1: 1,3-Benzothiazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
37%
Stage #1: 1,3-Benzothiazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere;
Stage #3: With hydrogenchloride In tetrahydrofuran; water
6.5 g
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-allyl-phenylamine
32704-22-6

2-allyl-phenylamine

5-Hydroxy-pentanoic acid (2-allyl-phenyl)-amide
114877-79-1

5-Hydroxy-pentanoic acid (2-allyl-phenyl)-amide

Conditions
ConditionsYield
With dimethylaluminum chloride In dichloromethane for 1h; Ambient temperature;99%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

tert-butyl(diphenyl)(2-propynyloxy)silane
110824-26-5

tert-butyl(diphenyl)(2-propynyloxy)silane

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one
137445-61-5

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one

Conditions
ConditionsYield
99%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

5-hydroxy-N,O-dimethyl-pentanohydroxamic acid
187756-41-8

5-hydroxy-N,O-dimethyl-pentanohydroxamic acid

Conditions
ConditionsYield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In dichloromethane at 0℃; for 0.333333h; Inert atmosphere;
Stage #3: With hydrogenchloride In dichloromethane; chloroform; water at 0℃; for 1h; Inert atmosphere;
99%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In hexane; dichloromethane at 0℃; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In hexane; dichloromethane at 0℃; Inert atmosphere;
Stage #3: With hydrogenchloride In hexane; dichloromethane; chloroform; water at 0℃;
92%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With trimethylaluminum In hexane; dichloromethane at 0℃; for 0.333333h;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In hexane; dichloromethane at 0℃; for 0.333333h;
92%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
25015-63-8

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

1,5-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)pentane

1,5-bis((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oxy)pentane

Conditions
ConditionsYield
With C12H36MgN2Si4 In neat (no solvent) at 20℃; for 0.25h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique;99%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

Tebbe's reagent

Tebbe's reagent

2-methylidenetetrahydropyran
38614-15-2

2-methylidenetetrahydropyran

Conditions
ConditionsYield
In benzene-d6 for 0.25h;99%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

(Z)-1-methoxybut-1-en-3-yne
2798-73-4, 3685-19-6, 3685-20-9

(Z)-1-methoxybut-1-en-3-yne

9-hydroxy-1-methoxynon-1-en-3-yn-5-one
112320-60-2

9-hydroxy-1-methoxynon-1-en-3-yn-5-one

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran at -78℃; for 1h;98%
With n-butyllithium 1) THF, -78 deg C, 50 min, 2) -78 deg C, 30 min; Yield given. Multistep reaction;
With n-butyllithium 1.) THF, hexane, -78 deg C, 1 h, 2.) -78 deg C, 1 h; Multistep reaction;
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

9-hydroxymethylanthracene
1468-95-7

9-hydroxymethylanthracene

poly(δ-valerolactone), asymmetric, telechelic, initiated by 9-anthracenemethanol/HCl*Et2O, Mn(NMR)=6900, Mw/Mn=1.1; monomer(s): δ-valerolactone; 9-anthracenemethanol

poly(δ-valerolactone), asymmetric, telechelic, initiated by 9-anthracenemethanol/HCl*Et2O, Mn(NMR)=6900, Mw/Mn=1.1; monomer(s): δ-valerolactone; 9-anthracenemethanol

Conditions
ConditionsYield
With hydrochloric acid diethyl ether In dichloromethane at 0℃; for 2h; Product distribution; Further Variations:; δ-valerolactone/9-anthracenemethanol ratio;98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-bromoethanol
540-51-2

2-bromoethanol

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-bromoethanol/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.10; monomer(s): δ-valerolactone; 2-bromoethanol

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-bromoethanol/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.10; monomer(s): δ-valerolactone; 2-bromoethanol

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether In dichloromethane at 0℃; for 2.5h;98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

butan-1-ol
71-36-3

butan-1-ol

poly(δ-valerolactone), initiated by 1-butanol/HCl*Et2O, Mn(exp)=19000, Mw/Mn=1.06; monomer(s): 1-butanol; δ-valerolactone

poly(δ-valerolactone), initiated by 1-butanol/HCl*Et2O, Mn(exp)=19000, Mw/Mn=1.06; monomer(s): 1-butanol; δ-valerolactone

Conditions
ConditionsYield
With hydrochloric acid diethyl ether In dichloromethane at 0℃; for 1.5h; Product distribution; Further Variations:; Temperatures; react. times; δ-VL/1-butanol rat.; init. δ-VL conc.; HCl/1-C4H9OH rat.;98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-hydroxyethyl acrylate
818-61-1

2-hydroxyethyl acrylate

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-hydroxyethyl acrylate/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.08; monomer(s): δ-valerolactone; 2-hydroxyethyl acrylate

poly(δ-valerolactone), asymmetric, telechelic, initiated by 2-hydroxyethyl acrylate/HCl*Et2O, Mn(NMR)=11000, Mw/Mn=1.08; monomer(s): δ-valerolactone; 2-hydroxyethyl acrylate

Conditions
ConditionsYield
With hydrogenchloride; diethyl ether In dichloromethane at 0℃; for 2.5h;98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

β‐cyclodextrin
7585-39-9

β‐cyclodextrin

polymer; monomer(s): β-cyclodextrin; δ-valerolactone

polymer; monomer(s): β-cyclodextrin; δ-valerolactone

Conditions
ConditionsYield
at 100℃; for 48h;98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

ethyl acetate
141-78-6

ethyl acetate

ethyl (3R)-3,7-dihydroxyheptanoate
529510-37-0

ethyl (3R)-3,7-dihydroxyheptanoate

Conditions
ConditionsYield
Stage #1: ethyl acetate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In tetrahydrofuran at -78℃; for 3h; Inert atmosphere;
Stage #3: With ruthenium trichloride; hydrogen; (+)-(R)-[2,3,2',3'-tetrahydro-5,5'-bi(1,4-benzodioxin)-6,6'-diyl]bis(diphenylphosphane) In ethanol at 80℃; under 7500.75 Torr; for 24h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;
98%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

2-methoxy-5-bromopyridine
13472-85-0

2-methoxy-5-bromopyridine

5-hydroxy-1-(6-methoxypyridin-3-yl)pentan-1-one
1134621-15-0

5-hydroxy-1-(6-methoxypyridin-3-yl)pentan-1-one

Conditions
ConditionsYield
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; regioselective reaction;
98%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃; Inert atmosphere; regioselective reaction;
98%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.25h;
Stage #2: 3,4,5,6-tetrahydro-2H-pyran-2-one In diethyl ether; hexane at -78 - 20℃;
85%
3,4,5,6-tetrahydro-2H-pyran-2-one
542-28-9

3,4,5,6-tetrahydro-2H-pyran-2-one

N,5-dihydroxypentanamide
59145-82-3

N,5-dihydroxypentanamide

Conditions
ConditionsYield
With hydroxylamine hydrochloride; potassium hydroxide In methanol at 0 - 20℃; Inert atmosphere;98%
With hydroxylamine hydrochloride; potassium hydroxide In methanol

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