Acetic Anhydride → HCID 54309198, compound

Participants

Reaction Steps

n-Butyl lithium (a 1.6M solution in hexane; 0.9 ml, 1.44 mmol) was added dropwise to a solution of 5-phenyl-1-pentyne (198.1 mg, 1.38 mmol) in tetrahydrofuran (4 ml) at 0° under argon. After 30 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (231 mg, 1.38 mmol) in tetrahydrofuran (1 ml) was added. Stirring was continued for 1 hour and acetic anhydride (0.4 ml) was added. After 2 hours, the mixture was poured into water and extracted thoroughly with ethyl ether. Evaporation of the dried (magnesium sulfate) extracts gave an oil, which was flash chromatographed on silica using 5% ethyl ether/hexane. Fractions with Rf of about 0.33 on evaporation gave the title ester as an oil.

Provenance & Evidence