Methyl heptanoate → 5-Hexylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester

HRID 616297Notes

Reaction equation

HRID 616297 reaction equation
CC(C)([O-:4])C.[K+].[CH2:7]([SH:13])[CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH3:14][O:15][C:16]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:17]>>[CH3:14][O:15][C:16]([CH:18]1[CH:22]([CH2:23][S:13][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:21][CH2:20][C:19]1=[O:4])=[O:17]

Participants

4

Reactant 3

HCID 7826Methyl heptanoateHCID 81061-HexanethiolHCID 23665647Potassium tert-butoxide

Product 1

HCID 542393645-Hexylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl esterYield 61.3%

Procedure

In accordance with the process of Example 17, potassium t-butoxide, (336 mg; 3 m mol), n-hexyl mercaptan (354 mg; 3 m mol) and 2-oxo-bicyclo 3.1.0!hexane-1-carboxylic acid methyl ester (463 mg; 3 m mol) were used to obtain 500 mg of 5-hexylthiomethyl-2-oxo-cyclopentanecarboxylic acid methyl ester.

Sources & evidence

ORD record
ord-6813b7b5544b483e9e3dd6ffc96b5d32
Source dataset
uspto-grants-1978_02
Patent number
US04073799

Reaction notes

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