Cyclohexanecarbonyl chloride → 4-[1-(Cyclohexanoyloxy)tridecyl]-2-trimethylsilylfuran

Participants

Reaction Steps

tert-Butyl lithium (a 1.7 M solution in pentane; 0.33 ml, 0.55 mmol) was added dropwise to a solution of 4-(1-hydroxytridecyl)-2-trimethylsilylfuran (170 mg, 0.50 mmol) in tetrahydrofuran (5 ml) at 0 degrees under argon. After 10 minutes, cyclohexanecarboxylic acid chloride (74 microliter, 0.55 mmol) was added. The mixture was stirred at room temperature for 15 hours and quenched with water. Extraction and evaporation of the dried (magnesium sulphate) extracts gave an oil, which was purified by preparative TLC (20×20 cm, 1000 u silica plate; developed with 5% ethyl ether/hexane). The title ester was obtained as a pale yellow oil.

Provenance & Evidence