Tetrabutylammonium Fluoride → HCID 58932222, compound

A solution of (8E,12E,14E)-3,21-bis(diethylisopropylsiloxy)-16-hydroxy-6,10,12,16,20-pentamethyl-7-((4-(1-methylpiperidin-4-yl)piperazin-1-yl)carbonyl)oxy-18,19-epoxytricosa-8,12,14-trien-11-olide (18.5 mg, 19.2 μmol) in tetrahydrofuran (2 mL) was cooled to 5° C. Tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 42.3 μL, 42.3 μmol) was added dropwise to the solution, and the reaction mixture was stirred at room temperature for four hours. 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 an aqueous solution of sodium hydrogencarbonate, dried over anhydrous magnesium sulfate, filtered concentrated under reduced pressure. The resulting residue was purified by thin-layer chromatography (Fuji Silysia NH Silica gel plate; methanol-dichloromethane, 1:24) to obtain the title compound (7.6 mg, 56%) as a colorless oil.