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

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Reaction Steps

To a stirred solution of 2.75 g (0.010 mol) of (naphthalene-1-sulfonyl)-acetic acid methyl ester in 100 mL of MeOH at RT, 0.19 mL (0.011 mol, 1.1 eq) of a solution of sodium methoxide (5.4 M in MeOH) were added. After 15 min, 1.1 g (0.011 mol, 1.1 eq) of 2-cyclohexen-1-one were added. The reaction mixture was stirred at RT for 3 hours followed by an additional 4 hours at 60° C., diluted with 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 (from 4:1 to 1:2) yielded 1.78 g (48%) of (naphthalene-1-sulfonyl)-(3-oxo-cyclohexyl)-acetic acid methyl ester as a racemic mixture of diastereomers, light orange oil, MS: 361 (MH+).

Provenance & Evidence