2-(Benzyloxy)-1-(3-butenyl)-3-methoxybenzene → (2S)-4-[2-(benzyloxy)-3-methoxyphenyl]-1,2-butanediol

Participants

Reaction Conditions

Reaction Steps

To a suspension of AD-mix-α (63.28 g) in water:tert-butyl alcohol (1:1, 300 mL) cooled to 0° C. was slowly added via an addition funnel to a solution of 2-(benzyloxy)-1-(3-butenyl)-3-methoxybenzene (12.13 g, 45.2 mmol) in water:tert-butyl alcohol (1:1, 300 mL) and the reaction mixture was allowed to stir at room temperature for 12 h. The reaction mixture was quenched by the addition of sodium sulfite. The reaction mixture was diluted with water (500 mL) and ethyl acetate (500 mL). The aqueous phase was separated and extracted with ethyl acetate (2×200 mL). The combined organic extracts were washed with aqueous sodium chloride (400 mL), dried (magnesium sulfate) and the solvent was removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, ethyl acetate:hexanes 4:1) gave 12.57 g (92%, 40% ee) of (2S)-4-[2-(benzyloxy)-3-methoxyphenyl]-1,2-butanediol as a colorless oil. [α]D25=−3.04 (c 10.2 in methanol, 40% ee); Rf=0.72 (silica, ethyl acetate:hexanes 4:1); Anal. Calcd. for C18H22O4.0.1 H2O: C, 71.08; H, 7.36. Found: C, 70.95; H, 7.33.

Provenance & Evidence