Pyridine → 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

Participants

Reaction Steps

To a solution of 3.06 g of 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenol and 1.50 g of triphosgene in 20 mL of CH2Cl2 cooled at −78° C. was added 1.2 mL of pyridine. The reaction mixture was warmed to rt. After 15–30 min, the white suspension was transferred to a solution containing 5.95 g of (2Z)-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-ene-1,4-diol and 1.5 mL of pyridine in 20 mL of CH2Cl2 at rt. The reaction was stirred at rt for 15 min. The reaction was quenched with aqueous 1N HCl, extracted with EtOAc and washed with brine, dried over sodium sulfate, evaporated, and purified by flash chromatography (50–70% EtOAc/hexane) to afford 1.26 g of the title compound as a yellow oil.

Provenance & Evidence