Tetrahydrofuran → HCID 67158615, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of copper (I) chloride (164 mg) in THF (4 mL) was stirred at 0° C. and treated with 3,4-dichlorophenylmagnesium bromide (0.5 M in THF, 3.3 mL). The mixture was stirred for 5 min, then was treated with a solution of methyl 2-methyl-6-oxocyclohex-1-enecarboxylic acid (prepared according to the procedure of Belmont, D. T. et al., J. Org. Chem. 1985, 50, 4102; 140 mg) in THF. The mixture was allowed to warm to rt over 30 min, then was cooled to 0° C. and treated with a 9:1 solution of saturated ammonium chloride-concentrated ammonium hydroxide. The mixture was extracted three times with ethyl acetate and the combined organic layers were washed with saturated aqueous ammonium chloride, dried over sodium sulfate and then concentrated under vacuum. The resulting residue was filtered through silica gel to provide methyl 2-(3,4-dichlorophenyl)-6-methylcyclohexanecarboxylate (153 mg). Mass spectrum m/z 316.44 (M+H+).

Provenance & Evidence