Pyridine → HCID 15723365, compound

Participants

Reaction Steps

A solution of 4-(12-t-butyldimethylsiloxydodecyl)-2-trimethylsilylfuran (0.46 g, 1.0 mmol) and pyridine (0.3 ml) in acetic anhydride (4 ml) was stirred at 0° under nitrogen for 1/2 hour, then 3.5 hours at room temperature. Approximately 1 ml saturated sodium bicarbonate solution was added to the reaction mixture, which was subsequently poured into ethyl ether and water. The organic portion was washed successively three times with water, once with saturated sodium bicarbonate solution, once with water, once with 10% copper sulfate solution, twice with water, once with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale oil. The acetate (20% ethyl ether/hexane) was purified by flash chromatography (silica, 7% ethyl ether/petroleum ether) to give a colorless oil.

Provenance & Evidence