(2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate → (2Z)-4-hydroxy-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate
Reaction equation
[C:1]([O:4][CH2:5]/[C:6](/[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1)=[C:7](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[CH2:8][O:9][Si](C(C)(C)C)(C)C)(=[O:3])[CH3:2]>CC#N.C1(C)C=CC=CC=1>[C:1]([O:4][CH2:5]/[C:6](/[C:23]1[CH:24]=[CH:25][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1)=[C:7](/[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)\[CH2:8][OH:9])(=[O:3])[CH3:2]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 50.5 g of (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate in 125 mL of MeCN, 10 mL of PyHF was added and the resulted mixture was stirred at rt for 1.5 hr. The reaction mixture was diluted with 600 mL of toluene and then loaded on silica gel column and eluted with EtOAc. The solvent was evaporated to afford 38.3 g of the titled compound. 1H NMR (acetone-d6, 500 M Hz): δ 7.68 (d, 2H), 7.32 (d, 2H), 7.15–7.00 (m, 5H), 5.20 (s, 2H), 4.62 (d, 2H), 4.09 (t, 1H, OH), 3.02 (s, 3H), 1.92 (s, 3 H),