Acetic Acid → HCID 86608519, compound

Participants

Reaction Conditions

Reaction Steps

(8E,12E,14E)-7-acetoxy-21-benzoyloxy-6-(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (89.1 mg, 108 μmol) was dissolved in methanol (3 mL), and the solution was cooled to 0° C. Potassium carbonate (30.2 mg, 219 μmol) was added to the reaction solution. The reaction solution was warmed to room temperature, and stirred at the same temperature for 3.5 hours. Acetic acid (12.3 μL, 215 μmol) was added to the reaction solution, and then the solution was concentrated. The concentrate was suspended in ethyl acetate (30 mL), and the suspension 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→4:1) to obtain the title compound (60.9 mg, 77.6 μmol, 72.1%) as a colorless oil.

Provenance & Evidence