Dodecyl acetate → HCID 22165559, compound

Participants

Reaction Steps

A solution of dodecyl acetate (240 mg, 1.04 mmol) in tetrahydrofuran (2 ml) was added to a solution of lithium diisopropylamide (1.04 mmol; =generated from 0.15 ml of diisopropylamine and 0.42 ml n-butyl lithium at -78°) in tetrahydrofuran (10 ml) at -78° under argon. After 1h, a solution of 5-triethylsilyl-3-furaldehyde (200 mg, 0.95 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 15h while the cooling bath attained room temperature. The mixture was quenched with water and was extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extracts gave an oil which was purified by a silica column using 20% ethyl ether/hexane to give the titled ester.

Provenance & Evidence