Tetrahydrofuran → HCID 19899112, compound

Participants

Reaction Steps

2.65 g of a mixture of methyltriphenylphosphonium bromide and sodium amide (approximately 6.3 mmol of each component) was stirred under nitrogen and 16 ml of dry tetrahydrofuran were added. After stirring at room temperature for 15 minutes, the mixture was cooled in ice and a solution of 1.85 g (5.79 mmol) of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-oxo-4H-cyclohept[d]isoxazole-7-carboxylate in 11 ml of dry tetrahydrofuran was added dropwise. The mixture was stirred in the cold for 0.5 hour and then at room temperature for 3 hours. The mixture was treated with 10 ml of saturated aqueous ammonium chloride solution and then partially evaporated. The aqueous phase was extracted three-times with dichloromethane and the combined organic phases were dried over magnesium sulfate and evaporated. The residue was triturated with diethyl ether. The solid was filtered off and washed with diethyl ether and the filtrate was evaporated. The residue was chromatographed on silica gel using 50% ethyl acetate/hexane for the elution. There were obtained 1.06 g of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylene-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 113°-114° C.

Provenance & Evidence