2,2,2-Trichloroethyl butyrate → 4-(Tetrahydropyran-2-yloxy)phenylethanol

Participants

Reaction Conditions

Reaction Steps

To 120 ml of anhydrous diethyl ether was added 22.2 g (0.1 mole) of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol, 22.4 g (0.1 mole) of 2,2,2-trichloroethyl butyrate and 25.2 g of Lipase P, and the mixture was reacted with stirring at 25° C. for 90 hours. After the reaction mixture was filtered by suction to remove Lipase P, the filtrate was concentrated, and the concentrate was then purified by silica gel chromatography [ethyl acetate/n-hexane=1/4 by volume] to give 10.2 g of S-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethanol (yield: 92%) and 13.1 g of R-form of 1-(4-(tetrahydro-2-pyranyloxy)phenyl)ethyl butyrate (yield: 91%).

Provenance & Evidence