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

HRID 1090328Notes

Reaction equation

HRID 1090328 reaction equation
[Si:1]([O:8][CH:9]([CH3:14])[CH2:10][C:11]([OH:13])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:15]1([SH:21])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:15]1([S:21][O:12][C:11](=[O:13])[CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH3:14])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 10868DicyclohexylcarbodiimideHCID 13712781(-)-3-t-Butyldimethylsilyloxybutyric acid

Product 1

HCID 54408146(-)-3-t-Butyldimethylsilyloxybutyric acid phenylthioesterYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.18 g (19.2 mmol) of (-)-3-t-butyldimethylsilyloxybutyric acid and 2.26 ml (22 mmol) of thiophenol dissolved in 100 ml of methylene chloride, 4.53 g (22 mmol) of N,N'-dicyclohexylcarbodiimide was added. After stirring the mixture at room temperature for 2 hours, the resultant was filtered and the filtrate was concentrated and distilled (110° to 116° C./0.3 mmHg) to give 5.00 g of (-)-3-t-butyldimethylsilyloxybutyric acid phenylthio ester (yield: 83%).

Workup

  1. filtrationthe resultant was filtered
  2. concentrationthe filtrate was concentrated
  3. distillationdistilled (110° to 116° C./0.3 mmHg)

Sources & evidence

ORD record
ord-eb65f810d83340cbb3498fc23a9f4963
Source dataset
uspto-grants-1992_01
Patent number
US05081238

Reaction notes

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