3-(4-chlorophenyl)-3-methylbutan-2-one

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 3-(4-chlorophenyl)-3-methyl-2-butanone (197 mg, 1 mmol) in diethyl carbonate (1.32 g, 11 mmol) was added at 20° C. under an atmosphere of nitrogen portion wise a dispersion of 55% sodium hydride in mineral oil (91 mg, 2.1 mmol). The reaction turned yellow and was heated to 50° C. After the gas evolution stopped the reaction was stirred at 85° C. for 30 min. After cooling to 20° C. the reaction was poured onto ice-water (2 mL) and then acetic acid (0.14 mL) was added. The reaction was extracted twice with diethyl ether. The combined organic layers were washed with water and with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using heptene/ethyl acetate (9:1 v/v) as eluent to yield the title compound as a pale-yellow oil (79 mg, 29%). After cooling to 20° C. the reaction was poured onto ice-water (2 mL) The reaction was extracted twice with diethyl ether The combined organic layers were washed with water and with brine dried over sodium sulfate evaporated under reduced pressure The residue was purified by column chromatography on silica gel