(-)-2,2,2-Trifluoro-1-(9-anthryl)ethanol → (1r)-1-Methylthiocarbonyloxyethyl benzoate

Participants

Reaction Steps

A mixture of 1-methylthiocarbonyloxyethyl benzoate (2g) (50 g) and lipase from Candida rugosa (2.50 g) in pH 7.2 phosphate buffered saline (500 mL) was stirred at room temperature. The reaction was monitored by 1H-NMR using the chiral solvating agent (R)-(−)-2,2,2-trifluoro-1-(9-anthryl)ethanol. The reaction was complete after ca. 12 hours. The reaction mixture was diluted with ether and the ether layer separated and filtered through a pad of CELITE® 545 to remove the enzyme. The ether layer was washed with aqueous sodium bicarbonate (NaHCO3) (5 times) and brine, and dried over anhydrous sodium sulfate (Na2SO4). After the solvent was removed by rotary evaporation, 22 g of the title compound (5) was obtained. 1H-NMR using a chiral solvating agent showed a single isomer and the absolute configuration was confirmed by derivatization to a compound having a known stereochemistry. 1H-NMR (CDCl3): δ 1.65 (d, J=5.6 Hz, 3H), 2.35 (s, 3H), 7.20 (q, J=5.6 Hz, 1H), 7.45 (m, 2H), 7.58 (m, 1H), 8.06 (m, 2H) ppm.

Provenance & Evidence