Acetic Anhydride → (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-enyl acetate
Reaction equation
[Si:1]([O:8][CH2:9]/[C:10](/[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[C:11](/[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)\[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:30](OC(=O)C)(=[O:32])[CH3:31]>CN(C1C=CN=CC=1)C.ClCCl>[C:30]([O:13][CH2:12]/[C:11](/[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1)=[C:10](/[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)\[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])(=[O:32])[CH3:31]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 46 g of (2Z)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-[4-(methylsulfonyl)phenyl]-3-phenylbut-2-en-1-ol with 120 mmol of DMAP in 1 L of dichloromethane, 120 mmol of acetic anhydride was added dropwise. The resulting mixture was stirred at rt for 1 hr. The reaction mixture was loaded on a silica gel column and eluted with EtOAc to afford 50.5 g of the titled compound as a white solid. 1H NMR (acetone-d6, 500 M Hz): δ 7.68 (d, 2H), 7.33 (d, 2H), 7.15–7.04 (m, 5H), 5.16 (s, 2H), 4.75 (s, 2H), 3.02 (s, 3H), 1.92 (s, 3H), 0.81 (s, 9 H), -0.03 (s, 6H).
Workup
- washeluted with EtOAc
Sources & evidence
- ORD record
- ord-cb10e75d6fc347c2967f63a41e73c344
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07169809B2
Reaction notes
Loading…