Acetic Anhydride → HCID 15723375, compound

Participants

Reaction Steps

Tert-butyl lithium (a 1.7M solution in hexane (1.27 ml, 2.16 mmol) was added to a -78° solution of 1-bromo-5-(1-naphthyl)-pentane (300 mg, 1.08 mmol) in tetrahydrofuran (2 ml) under nitrogen. After stirring for 30 minutes at -78°, a solution of 5-trimethylsilyl-3-furaldehyde (182 mg, 1.08 mmol) in tetrahydrofuran (0.5 ml) was added and the solution was stirred 2 hours at room temperature. Acetic anhydride (20 mg, 0.2 mmol) was added and the solution stirred at room temperature overnight. The reaction was quenched with water. Extraction (ethyl ether) and evaporation of the dried (magnesium sulfate) extracts gave an oil. Purification of the crude material by preparative TLC (developed with 10% ethyl ether/hexane) gave the title compound as a yellow oil.

Provenance & Evidence