Diethyl Ether → 2-(5-Bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-propan-2-ol

Participants

Reaction Steps

A stirred, cooled (ice bath) solution of 1-(5-bromo-3,3,6-trimethyl-2,3-dihydro-benzofuran-7-yl)-ethanone (Compound 48, 2.0 g, 7.09 mmol), was treated drop wise with a 3M solution of methylmagnesium bromide in diethylether (2.84 mL, 8.51 mmol) and the resulting reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was cooled (ice bath), quenched with saturated ammonium chloride solution and extracted with ether. The organic extract was washed with brine and dried over anhydrous sodium sulfate, filtered and evaporated to a residue which on flash column chromatography using 7% ethyl acetate in hexanes as the eluent afforded the title compound (I.51 g, 71.5%) as a white solid. 1H NMR (300 MHz, CDCl3): δ 7.21 (s, 1H), 4.35 (s, 1H), 4.22 (s, 2H), 2.53 (s, 3H), 1.67 (s, 6H), 1.31 (s, 6H).

Provenance & Evidence