Triethylamine → 5-Isoxazolecarboxylic acid, 3-(4-methylphenyl)-, methyl ester

Participants

Reaction Steps

Added to 100 ml of chloroform were 10.0 g (74.1 mmol) of 4-methylbenzaldoxime, 9.9 g (74.4 mmol) of N-chlorosuccinimde and 0.4 ml of pyridine. After N-chlorosuccinimide was completely dissolved, the resulting solution was stirred for further 30 minutes. Under ice cooling, 9.3 g (110.7 mmol) of methyl propionate and 9.0 g (89.1 mmol) of triethylamine were added. The resulting mixture was stirred at room temperature for 12 hours. The reaction mixture was added with water and then extracted with chloroform. The extract was treated by a method known per se in the art. Subsequent purification on a silica gel column (eluent: chloroform) gave 3-(4-methylphenyl)-5-methoxycarbonylisoxazole as crystals. Analytical results of the crystals obtained: Yield: 8.0 g (49.8%). Melting point: 106°-108° C.

Provenance & Evidence