1-Bromododecane → 3-(1-Hydroxytridecyl)-5-trimethylsilylfuran

Participants

Reaction Steps

A mixture of 1-bromododecane (2.97 g, 11.9 mmol) and magnesium turnings (300 mg, 12.5 mmol) in tetrahydrofuran (20 ml) was refluxed under argon for 30 minutes. On cooling, a solution of 5-trimethylsilyl-3-furaldehyde (1g, 5.9 mmol) in tetrahydrofuran (THF) (2 ml) was added. After 30 min., the reaction mixture was quenched with saturated ammonium chloride. Extraction (ethyl ether), drying (magnesium sulfate) and evaporation afforded an oil, which was purified by flash chromatography on silica using 15% ethyl ether/hexane. Fractions with Rf of about 0.25 on evaporation gave the title alcohol as a pale yellow oil, which solified into a colorless solid on storage at -20°.

Provenance & Evidence