Acetyl chloride → 6-Acetylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one

Participants

Reaction Steps

Acetyl chloride (142 μl, 1.8 mmol) was added to a solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexene-1-one (R. F. Parcell and J. P. Sanchez, J. Org. Chem., 46: 5055 [1981]), (200 mg, 0.9 mmol) and triethylamine (1.0 ml) in dichloromethane (10 ml), and the reaction stirred at room temperature for 1 h. Analysis by TLC indicated complete reaction, and the mixture was partitioned between ethyl acetate and 1N HCl. The organic phase was washed with brine, dried (MgSO4), and the solvent removed by evaporation. Flash chromatography on silica gel eluted with 1:1 ethyl acetate/hexane afforded 6-acetylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one which crystallized on standing, m.p. 144°-145° C.

Provenance & Evidence