Ethyl phenylacetate → 2-Phenylethanol

Participants

Reaction Conditions

Reaction Steps

To a dry Schlenk tube under argon was added 50 mg of titanocene dichloride (0.2 mmol) and 2 mL of tetrahydrofuran. The slurry was cooled to -78° C. in a dry ice/acetone bath and 200 μL of a 2M ether solution of pentylmagnesium bromide (0.4 mmol) was added. After stirring for 15 minutes, 930 μL of diphenylsilane (5.0 mmol) was added and the reaction mixture was allowed to warm to 0° C. Next 637 μL of ethyl 2-phenylethanoate (4.0 mmol) was then added and the reaction mixture was allowed to warm to room temperature. After 2 hours, an additional 200 μL of diphenylsilane was added and the reaction was stirred for 1.5 hours. The catalyst was then quenched by exposure to air until the color changed from dark brown to yellow. 5 mL of tetrahydrofuran and 15 mL of 1N NaOH in MeOH solution were then added. After stirring for 2 hours, the mixture was added to a brine/hexane mixture (150 mL each), shaken vigorously, and the layers were then separated. The aqueous layer was extracted with hexane (2×50 mL), the combined organic extracts were dried over MgSO4, filtered, and concentrated by rotary evaporation. The crude product was purified by flash chromatography (ether:hexane=3:7), which afforded 397 mg (81% yield) of phenethyl alcohol.

Provenance & Evidence