Acetic Anhydride → 4-(1-Acetoxytridecyl)-2-trimethylsilylfuran

Participants

Reaction Steps

A mixture of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (1.32 g, 3.89 mmol), acetic anhydride (4 ml) and pyridine (6 ml) was stirred under argon at ca. 20° for 16 h. After most of the solvent was removed under high vacuum (<40°), the residue was dissolved in ethyl ether (40 ml) and washed thoroughly with aqueous copper sulfate and water. Drying (magnesium sulfate) and evaporation gave a brown oil, which was flash chromatographed on silica using 5% ethyl ether/petroleum ether. Fractions with Rf of about 0.55 (10% ethyl ether/petroleum ether) on evaporation gave the desired trimethylsilylfuran as a pale yellow oil.

Provenance & Evidence