(-)-3-t-Butyldimethylsilyloxybutyric acid phenylthioester → (-)-3-Hydroxybutyric acid phenylthioester

HRID 1090329Notes

Reaction equation

HRID 1090329 reaction equation
[C:1]1([S:7][O:8][C:9](=[O:21])[CH2:10][CH:11]([O:13][Si](C(C)(C)C)(C)C)[CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C.C1COCC1.O>[C:1]1([S:7][O:8][C:9](=[O:21])[CH2:10][CH:11]([OH:13])[CH3:12])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 54408146(-)-3-t-Butyldimethylsilyloxybutyric acid phenylthioester

Product 1

HCID 53886232(-)-3-Hydroxybutyric acid phenylthioesterYield 94%

Reagents, catalysts & solvents 1

HCID 21877175AcOH THF waterSolvent

Conditions

Temperature
50 °C

Procedure

To 3.26 g (10.4 mmol) of (-)-3-t-butyldimethylsilyloxybutyric acid phenylthio ester was added 50 ml of acetic acid: THF:water (3:1:1) and the mixture was stirred at 50° C. for 24 hours. The resultant was concentrated and distilled (128° to 130° C./0.8 mmHg) to give 1.91 g of (-)-3-hydroxybutyric acid phenylthio ester (yield: 94%).

Workup

  1. concentrationThe resultant was concentrated
  2. distillationdistilled (128° to 130° C./0.8 mmHg)

Sources & evidence

ORD record
ord-1ad6a6c7ae2049f7b6f8f5e35693f85f
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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