Vinyl Acetate → HCID 10518044, compound

Participants

Reaction Conditions

Reaction Steps

To 31.98 g of (2RS,3SR)-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentan-2-ol in 320 ml of vinyl acetate, 15.1 ml of triethylamine was added. The resulting reaction solution was stirred with 1.0 g of immobilized lipase (Toyozyme LIP) at 30° C. for 16 hours. After 0.9 g of immobilized lipase was further added, the solution was stirred at the same temperature for 46 hours. The insolubles were filtered off, and the filtrate was diluted with ethyl acetate, washed successively with 1N hydrochloric acid, saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography [hexane/ethyl acetate=5/1→1/1] to give 18.40 g of (2R,3S)-2-acetoxy-5,5-diethoxy-3-(3,4-methylenedioxyphenyl)pentane and 16.05 g of the title compound as colorless oily substances.

Provenance & Evidence