Benzyl mercaptan → 5-Benzylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester

HRID 616296Notes

Reaction equation

HRID 616296 reaction equation
CC(C)([O-:4])C.[K+].[CH2:7]([SH:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:15][O:16][C:17]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:18]>>[CH3:15][O:16][C:17]([CH:19]1[CH:23]([CH2:24][S:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:22][CH2:21][C:20]1=[O:4])=[O:18]

Participants

4

Reactant 3

HCID 7509Benzyl mercaptanHCID 7826Methyl heptanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 540315235-Benzylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl esterYield 78%

Procedure

In accordance with the process of Example 16, potassium t-butoxide (336 mg; 3 m mol), benzyl mercaptan (372 mg; 3 m mol) and 2-oxo-bicyclo 3.1.0! hexane-1-carboxylic acid methyl ester (463 mg; 3 m mol) were used in the reaction, and the reaction product was purified by a silica gel column chromatography with ethyl acetate and n-hexane (1.5; 8.5) to obtain 650 mg of 5-benzylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester as an oil.

Workup

  1. customthe reaction product was purified by a silica gel column chromatography with ethyl acetate and n-hexane (1.5; 8.5)

Sources & evidence

ORD record
ord-9ddf21f58ffd4e66a86d7463b454d7de
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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