Aluminium lithium hydride → HCID 86698785, compound

Participants

Reaction Steps

To a 0° C. suspension of LAH (444 mg, 11.1 mmol) in diethyl ether (10 mL) was added a solution of 2-Benzyloxymethyl-2-(4-bromo-phenyl)-malonic acid diethyl ester (1.67 g, 3.84 mmol) in diethyl ether (10 mL) dropwise via addition funnel. The reaction mixture was warmed to room temperature and stirred for 22 hours. The reaction was quenched with water (1.5 mL), 15% NaOH (1.5 mL), and water (3 mL) added sequentially. The white slurry was stirred for 30 minutes, diluted with ethyl acetate and filtered to remove the aluminum salts. The filtrate was concentrated in vacuo to afford a green semisolid, which was purified by flash chromatography (40 g silica, 30-82% ethyl acetate/heptane, 10 column volumes). Product fractions were combined and concentrated in vacuo to afford the title compound as a colorless oil (482 mg, 36% yield). 1H NMR (500 MHz, CD3OD) δ ppm 7.45 (d, J=8.54 Hz, 2 H), 7.35 (d, J=8.78 Hz, 2 H), 7.22-7.33 (m, 5 H), 4.51 (s, 2 H), 3.92 (s, 4 H), 3.82 (s, 2 H).

Provenance & Evidence