Triethylamine → HCID 86601417, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (8E,12E,14E)-3,21-bis(diethylisopropylsiloxy)-7,16-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (271 mg, 0.3605 mmol), 4-dimethylaminopyridine (22 mg, 0.18 mmol) and triethylamine (369 mg, 3.61 mmol) in methylene chloride (5 mL) was cooled to 5° C. A solution of 4-nitrophenyl chloroformate (374 mg, 1.8 mmol) in methylene chloride (3 mL) was added dropwise to the solution, and the reaction mixture was stirred at 5 to 10° C. for one hour. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with an aqueous solution of sodium hydrogencarbonate. The resulting organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:9->1:7->1:6) to obtain the title compound (319.6 mg, 97%) as a yellow pale oil.

Provenance & Evidence