2-Cyclohexen-1-one → Benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester

Participants

Reaction Steps

To a stirred solution of 9 g (0.042 mol) of methyl phenylsulfonylacetate in 90 mL of MeOH at 0° C., 1.56 mL (0.008 mol, 0.2 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 4.04 g (0.02 mol) of 2-cyclohexen-1-one were added. The reaction mixture was allowed to reach RT within 4 hours, diluted with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic phases were dried over Na2SO4, filtered and evaporated. Column chromatography on silica gel with heptane/EtOAc 1:1 yielded 11.50 g (88%) of benzenesulfonyl-(3-oxo-cyclohexyl)-acetic acid methyl ester as a racemic mixture of diastereomers, light yellow oil, MS: 311 (MH+).

Provenance & Evidence