4-Phenylbutanoyl Chloride → 4-[1-(4-Phenylbutanoyloxy)tridecyl]2-trimethylsilylfuran

Participants

Reaction Steps

tert-Butyl lithium (a 1.7 M solution in pentane; 0.47 ml, 0.79 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (256.4 rag, 0.76 mmol), prepared as in Example 38, in tetrahydrofuran (5 ml) at -78 degrees under argon. After 10 minutes, a solution of 4-phenylbutyryl chloride (145 mg, 0.79 mmol) was added. Stirring was continued at room temperature for 2 days and the mixture was quenched with water. Extraction and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative thin-layer chromatography (20×20 cm, 1000 micron silica plate; developed with 10% ethyl ether/hexane). The title ester was obtained as a light yellow oil.

Provenance & Evidence