Triethylamine → HCID 86601414, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (8E,12E,14E)-7-hydroxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (38.6 mg, 0.046 mmol), 4-dimethylaminopyridine (26 mg, 0.207 mmol) and triethylamine (28 mg, 0.276 mmol) in methylene chloride (2 mL) was cooled to 5° C. A solution of 4-nitrophenyl chloroformate (29 mg, 0.138 mmol) in methylene chloride (1 mL) was added to the reaction mixture, and the reaction mixture was stirred at 5° 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 organic layer was sequentially washed with an aqueous solution of ammonium chloride, an aqueous solution of sodium hydrogencarbonate and water, dried with anhydrous magnesium sulfate, and filtered. Then, the filtrate was 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, 1:14) to obtain the title compound (46.1 mg, 100%) as a yellow pale oil.

Provenance & Evidence