Aluminium lithium hydride → HCID 69057883, compound

Participants

Reaction Steps

A solution of 3-(2-benzyloxy-4-ethyl-phenyl)-acrylic acid ethyl ester (2.9 g, 9.3 mmol) dissolved in ether (7 mL) was added to a cooled 0° C. suspension of lithium aluminium hydride (0.89 g, 23.4 mmol) in ether (20 mL). The reaction mixture was stirred for 4 hours, quenched with H2O (3.6 mL) and 15% NaOH (0.9 mL) and then filtered through glass frit washing with ether. The filtrate was concentrated to a clear oil and purified by flash column chromatography (0% to 30% EtOAc in hexanes) to give the product (1.78 g, 71%). 1H NMR (400 MHz, CDCl3): δ 6 1.22 (t, J=7.6 Hz, 3 H), 2.62 (q, J=7.6 Hz, 2 H), 4.29 (m, 2 H), 5.10 (s, 2 H), 6.35 (dt, J=16.2, 7.6 Hz, 1 H), 6.78 (s, 1 H), 6.80 (d, J=7.1 Hz, 1 H), 6.95 (d, J=16.2 Hz, 1 H), 7.32–7.45 (m, 6 H).

Provenance & Evidence