Tetrahydrofuran → HCID 10496372, compound

Participants

Reaction Steps

Oxalyl chloride (11.3 g) and DMF (3 drops) were successively added dropwise to a solution of 2-(carboxy)(phenyl)methylthio-3-(4-methylphenyl)propionate (25.5 g) in tetrahydrofuran (THF) (150 ml), followed by stirring for 1.5 hours at room temperature and concentrated under reduced pressure. The residual oil was dissolved in dichloromethane (50 ml). The solution was added dropwise to a suspension of aluminum chloride (AlCl3)(21.7 g) and dichloromethane (200 ml) with ice-cooling. The reaction mixture was stirred for 2 hours with ice-cooling and poured into ice-water. The dichloromethane layer was separated, washed with water, dried (MgSO4) and distilled off to give crystals of methyl trans-7-methyl-5-oxo-4-phenyl-1,2,4,5-tetrahydro-3-benzothiepine-2-carboxylate (7.2 g, 30%). Recrystallization from ethyl acetate-hexane gave colorless prisms.

Provenance & Evidence