Acetic Anhydride → HCID 19885981, compound

Participants

Reaction Steps

n-Butyl lithium (a 1.6M solution in hexane; 0.46 ml, 0.74 mmol) was added dropwise to a solution of (2-pyridyl)propyl tributylstannyl ether (309.2 mg, 0.70 mmol) in tetrahydrofuran (5 ml) at -78° under argon. After 5 minutes, a solution of 5-trimethylsilyl-3-furaldehyde (118 mg, 0.70 mmol) in tetrahydrofuran (1.5 ml) was added, followed by acetic anhydride (0.1 ml, 1.05 mmol) after 1 hour. Stirring was continued at -78° for 4 hours and the mixture was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was flash chromatographed on silica using 40% ethyl acetate/hexane. Fractions with Rf of about 0.12 on evaporation afforded the title ester as a yellow oil.

Provenance & Evidence