Tetrabutylammonium Fluoride → HCID 178520927, compound

Participants

Reaction Steps

cis/trans-[4-(2,4-Bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl]methanol (24 mg) was dissolved in THF (5 ml), and tetrabutylammonium fluoride (0.12 ml, 1.0M in THF) was added. The resulting solution was stirred at room temperature for 15 hr and then partitioned between ethyl acetate (20 ml) and water (2 ml). The aqueous phase was extracted with ethyl acetate (3×20 ml) and the combined organic phases were washed with brine (20 ml), dried over anhydrous magnesium sulphate, and concentrated in vacuo. Purification via flash column chromatography (SiO2 eluting with ethyl acetate:petroleum ether, 1:1 v/v) furnished the desired compound (7 mg, 59%) as a white solid. δH (CD3OD): 0.95-1.06 (0.5H, m), 1.24-1.38 (0.5H, m), 1.43-1.60 (4H, m), 1.69-1.83 (4H, m), 2.62-2.77 (1H, m), 3.30 (1H, d), 3.56 (1H, d), 6.11-6.17 (2H, m), 6.76-7.01 (1H, m); m/z (ES−) 281 (M−1+60)−.

Provenance & Evidence