Aluminium lithium hydride → 2-(2-(Allyloxy)ethoxy)ethanol

Participants

Reaction Steps

To a stirred solution of ester (8) (9.77 g, 55.1 mmol, 1.0 equiv.) in THF (100 mL) was carefully added one portion of LAH (95%, 1.10 g, 27.5 mmol, 0.5 equiv.) at 0° C. After 30 min, another portion of LAH was carefully added and the reaction was stirred for an additional 30 min. The reaction was then carefully quenched with a Na2SO4-saturated aqueous solution. The resulting white aluminum salts were then filtered off over a short plug of Celite (EtOAc washings) and the filtrate was evaporated under reduced pressure. Purification was achieved by Kugelrohr distillation under reduced pressure and provided 7.99 g (99%) of alcohol (9) as a colorless oil; bp>200° C. (water tap vacuum). Spectroscopic data were consistent with those reported in the literature.26 1H NMR (400 MHz, CDCl3) δ 5.92 (m, 1H), 5.28 (m, 1H), 5.19 (m, 1H), 4.04 (m, 2H), 3.73 (m, 2H), 3.68 (m, 2H), 3.62 (m, 4H), 2.36 (brs, 1H).

Provenance & Evidence