Ethyl Acetate → HCID 86608522, compound

Participants

Reaction Conditions

Reaction Steps

(8E,12E,14E)-7-acetoxy-6,21-dihydroxy-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (201 mg, 309 μmol) was dissolved in methylene chloride (2 mL). Triethylamine (220 μL, 1.58 μmol) and dimethylaminopyridine (17.0 mg, 139 μmol) were added to the reaction solution, and the reaction solution was cooled to 0° C. A solution of 4-nitrophenyl chloroformate (125 mg, 620 μmol) in methylene chloride (2 mL) was added to the solution. The reaction solution was warmed to room temperature, and then stirred for five hours. 4-nitrophenyl chloroformate (50.0 mg, 248 μmol) was further added to the reaction solution, and the solution was stirred at room temperature for two hours. The reaction solution was diluted with ethyl acetate (30 mL), and the dilution was washed with saturated aqueous solution of sodium hydrogencarbonate (6 mL) twice, purified water (6 mL) twice, and brine (6 mL). The resulting organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated. The concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1→3:1) to obtain the title compound (246 mg, 302 μmol, 97.6%) as a colorless oil.

Provenance & Evidence