Benzaldehyde → 1-Phenylethanol, (R)-

Participants

Reaction Steps

To a vial containing aminoalcohol 1 (0.05 g, 0.17 mmol) prepared as in Example 1 was added a solution containing benzaldehyde (0.32 g, 3.0 mmol), toluene (3.0 mL), and 1 M dimethylzinc in heptane (6.0 mL). After 3 days at room temperature, the mixture was diluted in ether (50 mL) and the reaction was quenched by dropwise addition of half-saturated aqueous ammonium chloride (50 mL). The ether layer was separated and the aqueous layer was further extracted with ether (2×50 mL). The combined ether layers were dried over magnesium sulfate whereupon the solvent was removed at reduced pressure. The residue was purified by flash chromatography on 220-400 mesh silica with 70% hexane and 30% ethyl acetate as eluant. The solvent was distilled to afford (R)-(+)-sec-phenethyl alcohol (0.27 grams, 73%) with spectroscopic properties identical to a commercial sample. [α]D25=+55.3, c=1.96 g/100 mL chloroform indicating enantiomeric excess was 99%.

Provenance & Evidence