Water → HCID 18617744, compound

Participants

Reaction Steps

To a cooled solution (0° C.) of (1M)lithium aluminum hydride (13.3 mL, 13.3 mmol) in THF (27 mL) is added a solution of 2-(4-furan-2-yl-phenyl)-2-propionic acid methyl ester (3.1 g, 12.7 mmol) (reference example 30a) in THF (11 mL). The resulting solution is stirred for 15 min then added slowly H2O (0.5 mL), 15% NaOH (0.5 mL) and H2O (1.5 mL). The resulting slurry is diluted with ether, filtered through a pad of celite and the filtrate concentrated to give 2.7 g of title compound as a white crystalline solid. 1H NMR (CDCl3) δ 1.34 (s, 6H), 3.62 (m, 3H), 6.46 (m, 1H), 6.62 (d, J=3 Hz, 1H), 7.40 (d, J=8 Hz, 2H), 7.46 (bs, 1H), 7.64 (d, J=8 Hz, 2H). MS (EI) m/z 216 (M+).

Provenance & Evidence