Tetrahydrofuran → HCID 23284516, compound

Participants

Reaction Steps

A tetrahydrofuran (30 ml) solution of 2-chloro-6-methylnicotinic acid (3.43 g, 20 mmol) was cooled to -40° C., mixed with ether (30 ml) solution of 2.0 M cyclohexyl magnesium chloride and stirred overnight at room temperature. The reaction solution was poured into saturated ammonium chloride aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration, the filtrate was concentrated under a reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give 2-chloro-3-cyclohexylcarbonyl-6-methylpyridine (650 mg, 14%) as a brown oily material.

Provenance & Evidence