Aluminium lithium hydride → (4-Phenylbicyclo[2.2.2]oct-1-yl)methanol

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 4-phenylbicyclo[2.2.2]octane-1-carboxylate (207 g, 801 mmol) in THF (850 mL) was added to a stirred solution of lithium aluminium hydride (20 g, 527 mmol) in THF (1.25 L) under nitrogen, maintaining a temperature of 20-25° C. with an ice/water bath. The reaction mixture was stirred for 3 h, allowed to stand overnight, then quenched by addition to a mixture of water (900 mL) and ice (300 g). The mixture was acidified to pH 1-2 with concentrated hydrochloric acid then extracted with ethyl acetate (3×1 L). The combined organics were dried (MgSO4) and evaporated down to give the title compound as a brown solid (176 g; ˜100%). 1H NMR (CDCl3) 1.35 (1H, brd s), 1.40-1.52 (6H, m), 1.71-1.85 (6H, m), 3.25 (2H, s), 7.05-7.13 (1H, m), 7.17-7.30 4H, m).

Provenance & Evidence