1,2-Dibromoethane → HCID 19885911, compound

Participants

Reaction Steps

To a stirred solution of 6-(benzo[b]thien-2-yl)hexylmagnesium bromide (1.22 mmol, prepared from 1.22 mmol 6-(benzo[b]thien-2-yl)-1-bromohexane and 2.44 mmol magnesium, initiated with a catalytic amount of 1,2-dibromoethane) in 1.5 ml tetrahydrofuran at 0° under argon was added dropwise 5-trimethylsilyl-3-furaldehyde (0.167 g., 0.99 mmol) in 1 ml tetrahydrofuran. This solution was allowed to warm to room temperature, stirred for 30 minutes, and then quenched with a 5% ammonium chloride solution. The resulting mixture was partitioned between ethyl ether and 5% sodium bicarbonate. The organic portion was washed with water, saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated to give a pale yellow oil. This material was purified by flash chromatography (silica, 100% hexane to 20% ethyl acetate/hexane) to give the desired alcohol.

Provenance & Evidence