Triethylamine → HCID 86601412, compound

Participants

Reaction Steps

A solution of (8E,12E,14E)-7-acetoxy-3,16,21-trihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (54 mg, 0.1 mmol), 4-dimethylaminopyridine (124 mg, 1 mmol), and triethylamine (102 mg, 1 mmol) in methylene chloride (2.5 mL) was cooled to 5° C. A solution of triethylsilyl chloride (152 mg, 1 mmol) in methylene chloride (0.5 mL) was added dropwise to the reaction mixture, and then the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with water. The resulting organic layer was 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, 1:19->1:14) to obtain the title compound (77.1 mg, 88%) as a colorless oil.

Provenance & Evidence