Ammonium Chloride → HCID 86653595, compound

Participants

Reaction Conditions

Reaction Steps

A stirred suspension of copper (I) iodide (213 mg) in diethyl ether (10 mL) at 0° C. was treated with methyllithium (1.6 M, 1 equivalent), forming a cloudy yellow mixture. Additional methyllithium (1.6 M, 1 equivalent) was added, forming a cloudy grey mixture. This cloudy grey mixture was stirred at 0° C. for 15 min, and then treated with a solution of methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-2-(diethoxyphosphoryloxy)-4,6-dimethylcyclohexen-1-carboxylate (130 mg) in diethyl ether (5 mL). A deep red color formed over 30 min. Stirring was continued while warming to rt for 2 h more. At the conclusion of this period, the resulting mixture was treated with 3:1 saturated aqueous ammonium chloride/concentrated ammonium hydroxide, and stirred for 10 min. The mixture was then extracted three times with diethyl ether, and the combined organic layers were washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over magnesium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel, eluting with 15% ethyl acetate/hexanes, to provide methyl (4RS,6RS)-6-(3,4-dichlorophenyl)-2,4,6-trimethylcyclohex-1-enecarboxylate (57 mg). Mass spectrum m/z 349.17 (M+Na+).

Provenance & Evidence