Sodium methanethiolate → HCID 67896175, compound

Participants

Reaction Steps

0.5 g (1.3 mmol) of a cis/trans mixture of methyl 4-bromo-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isoxazole-7-carboxylate (prepared as described in Example 9) in 5 ml of dry dimethylformamide was stirred, cooled in ice and treated with 0.15 g (2.1 mmol) of sodium methanethiolate. The mixture was stirred at room temperature for 24 hours and then evaporated. The residue was partitioned between water and dichloromethane and the organic phase was dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel using dichloromethane for the elution and there were obtained 0.028 g of methyl cis-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylthio-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 110°-112° C. and 0.041 g of methyl trans-3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4-methylthio-4H-cyclohept[d]isoxazole-7-carboxylate of melting point 127°-128° C.

Provenance & Evidence