Imidazole → (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol

Participants

Reaction Conditions

Reaction Steps

To a solution of 110 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and of imidazole in 1 L of THF stirred at −78° C., a solution 51 g of TBSCl in 250 mL of dichloromethane was added dropwise. The resulting mixture was stirred at −78° C. 0.5 hr. Brine was then added and then warmed to room temperature. The organic phase was separated and the aqueous phase was extracted with EtOAc. The organic phases were combined and dried over Na2SO4 and evaporated. The resulting crude material was purified by flash chromatography to afford 25.6 g of the title compound as a white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.69 (d, 2H), 7.37 (d, 2H), 7.18–7.04 (m, 5H), 4.77 (s, 2H), 4.65 (d, 2H), 3.96 (t, 1H, OH), 3.03 (s, 3H), 0.84 (s, 9H), 0.01 (s, 6H).

Provenance & Evidence