Diethyl Ether → HCID 22731324, compound

Participants

Reaction Steps

A stirred, cooled (ice-bath) solution of 5-bromo-3,3-dimethyl-2,3-dihydrobenzofuran-7-carbaldehyde (Intermediate 30, 1.72 g, 6.74 mmol) in 15 mL of anhydrous tetrahydrofuran was treated with a 1M solution of tert-butyl magnesium chloride solution in ether (6.74 mL, 6.74 mmol). The reaction mixture was then allowed to warm to room temperature and stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic phase was dried over anhydrous sodium sulfate, filtered and evaporated to an oil that on flash column chromatography using 5% ethyl acetate in hexane as the eluent afforded the title compound (0.95 g, 45%).

Provenance & Evidence