Isopropenyl acetate → HCID 53866555, compound

Participants

Reaction Steps

A mixture of (RS)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (221 g), isopropenyl acetate (380 ml) and lipase PS (Amano) (221 g) in diisopropyl ether (4.8 l) was stirred at ambient temperature for 4 days. The reaction mixture was filtrated (celite) and evaporated under reduced pressure. The residue was purified by flash chromatography (silica gel, using dichloromethane and dichloromethane-methanol (20:1) successively as eluents). The first eluate gave (R)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl acetate (138.2 g) as a pale yellow oil and the second eluate (S)-3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol (104.4 g) as a colorless powder.

Provenance & Evidence