1-Phenylethanol → Acetate

Participants

Reaction Steps

1-Phenylethanol (100 mg) was dissolved in a 10% solution of ethoxyvinyl acetate in hexane (2 ml), followed by addition of lipase PS (10 mg). After about 3 hours at room temperature, 50% conversion was observed by TLC. The alcohol and acetate were isolated using flash chromatography on silica gel 60 using a 1:10 to 1:1 gradient of ethyl acetate in hexane. The isolated yield of the acetate was 40%, corresponding to 80% of the theoretical maximum at 50% conversion, and that of the alcohol 39%. The enantiomeric excess (ee) of the acetate was >95% (determined by 1H-NMR, chiral shift experiment with Eu(hfc)3, 10 mg of acetate, 40 mg of shift reagent); αD +103.5° (c=1, MeOH).

Provenance & Evidence