5-bromopentyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate → 5-bromopentyl (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate

Participants

Reaction Steps

A mixture of 5-bromopentyl (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl carbonate (1 eq) and PyrHF (excess) in MeCN (0.25 M) was stirred at rt for 2 h, diluted with 5 volumes of toluene, filtered through a pad of silica gel eluted with 70% EtOAc/hexanes to give the titled compound.

Provenance & Evidence