5-(Trimethylsilyl)furan-3-carbaldehyde → HCID 19885934, compound

Participants

Reaction Steps

To a stirred solution of 9-phenylnonylmagnesium bromide (1.35 mmol, prepared from 0.383 g, 1.35 mmol of 1-bromo-9-phenylnonane and 4.11 mmol magnesium) in tetrahydrofuran (5 ml) at 0° under argon was added dropwise, 5-trimethylsilyl-3-furaldehyde (0.227 g, 1.35 mmol) in tetrahydrofuran (3 ml). The solution was warmed to room temperature and stirred for 30 minutes, quenched with 5% ammonium chloride and extracted into ethyl ether. The organic portion was washed with saturated sodium bicarbonate, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a yellow oil. Purification by flash chromatography (silica, 5 to 20% ethyl acetate/hexane) gave the desired alcohol.

Provenance & Evidence