Benzaldehyde → (R)-(+)-1-Phenyl-1-propanol

Participants

Reaction Steps

A solution of (1S,2R,4R)-(7,7-dimethyl-2-morpholinobicyclo[2.2.1]heptan-1-yl)methanethiol hydrochloride (MITH•HCl; (Ib)) (58 mg, 0.20 mmol) in n-heptane (10 mL) was extracted with 1 M Na2CO3 (10 mL). After separation of layers, the n-heptane layer was washed with 10% aq. NaCl (5 mL) and concentrated. The residual oil was co-evaporated with n-heptane (10 mL) to give MITH free base as a colorless oil. To the oil was added diethylzinc (3.0 mmol, 1.0 M in hexanes) at ambient temperature, and the mixture was stirred for 10 minutes. Neat benzaldehyde (200 μL, 2.0 mmol) was added in one portion at 0° C. Upon complete consumption of benzaldehyde as judged by TLC, sat. aq. NH4Cl (3 mL) was slowly added to the reaction product mixture followed by ethyl acetate (20 mL). The mixture was washed twice with 1 N aq. HCl (20 mL each) and brine (5 mL), dried over solid Na2SO4 and concentrated to give a colorless oil which was purified by silica gel column chromatography (1:10 ethyl acetate/n-heptane) to give (R)-1-phenyl-propanol as a colorless oil (232 mg; 85%; 96.3% e.e.).

Provenance & Evidence