Tetrabutylammonium Fluoride → HCID 12000037, compound

Participants

Reaction Steps

To a solution of (R)-3-(3,4-dimethoxybenzyloxy)-1-triisopropylsiloxy-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-propane (8) (20.0 mg, 27.3 μmol, 1.00 eq.) in dry tetrahydrofuran (0.55 mL) was added 1 M tetrabutylammonium fluoride solution in tetrahydrofuran (41 μL, 40.9 μmol, 1.50 eq.) at 0° C. After being stirred at the same temperature for 1 h, the reaction mixture was poured into brine. The aqueous layer was extracted with two portions of ethyl acetate. The combined extract was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:ethyl acetate=55:45) to give (S)-3-(3,4-dimethoxybenzyloxy)-2-[(2Z,6E,13E)-3,8,8,14,18-pentamethyl-11-methylene-nonadeca-2,6,13,17-tetraen-1-yloxy]-1-propanol (9) (15.4 mg, 26.4 μmol, 97%) as a colorless oil.

Provenance & Evidence