Acetic Acid → (-)-3-Hydroxybutyric acid phenylthioester

HRID 247701Notes

Reaction equation

HRID 247701 reaction equation
C(O)(=O)C.C1COCC1.[C:10]1([S:16][O:17][C:18](=[O:30])[CH2:19][CH:20]([O:22][Si](C(C)(C)C)(C)C)[CH3:21])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>O>[C:10]1([S:16][O:17][C:18](=[O:30])[CH2:19][CH:20]([OH:22])[CH3:21])[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 54408146(-)-3-t-Butyldimethylsilyloxybutyric acid phenylthioester

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

There was added 50 ml of a mixture of acetic acid, THF and water (3:1:1) to 3.26 g (10.4 mml) of (-)-3-t-butyldimethylsilyloxybutyric acid phenylthioester and the mixture was stirred at 50° C. for 24 hours. The obtained reaction mixture was concentrated and distilled at 128° to 130° C. under a pressure of 0.8 mmHg to give 1.91 g of (-)-3-hydroxybutyric acid phenylthioester.

Workup

  1. customThe obtained reaction mixture
  2. concentrationwas concentrated
  3. distillationdistilled at 128° to 130° C. under a pressure of 0.8 mmHg

Sources & evidence

ORD record
ord-a8cb2faf215f46e2812383ae3605d68c
Source dataset
uspto-grants-1987_11
Patent number
US04709064

Reaction notes

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