[3-(Tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxyphenyl)-methanol → [3-(Tert-butyldimethylsilanyloxy)-4-methoxyphenyl]-(3,5-dimethoxyphenyl)methanone
Reaction equation
[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([CH:15]([C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH3:26])[CH:18]=2)[OH:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[C:1]([Si:5]([CH3:28])([CH3:27])[O:6][C:7]1[CH:8]=[C:9]([C:15]([C:17]2[CH:18]=[C:19]([O:25][CH3:26])[CH:20]=[C:21]([O:23][CH3:24])[CH:22]=2)=[O:16])[CH:10]=[CH:11][C:12]=1[O:13][CH3:14])([CH3:3])([CH3:2])[CH3:4]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanol (13.1 g, 32.4 mmol) in CH2Cl2 (330 mL) was added manganese dioxide (13.0 g, 150.0 mmol), and the mixture was stirred at ambient temperature for 8 h. Manganese dioxide (13.0 g, 150.0 mmol) was again added, and stirring proceeded for an additional 16 h. The mixture was filtered through Celite, and the sicciate was washed with CH2Cl2 (50 mL). The filtrate was evaporated, providing [3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-phenyl]-(3,5-dimethoxy-phenyl)-methanone as an oil (12.9 g, 99% yield): 1H NMR (CDCl3) δ 0.18 (s, 6H, 2SiCH3), 1.00 (s, 9H, SiC(CH3)3), 3.83 (s, 6H, 2OCH3), 3.89 (s, 3H, OCH3), 6.65 (t, J=2.4 Hz, 1H, Ar), 6.86-6.90 (m, 3H, Ar), 7.39-7.47 (m, 2H, Ar).
Workup
- stirringstirring
- waitproceeded for an additional 16 h
- filtrationThe mixture was filtered through Celite
- washthe sicciate was washed with CH2Cl2 (50 mL)
- customThe filtrate was evaporated
Sources & evidence
- ORD record
- ord-4e5bc64bddcc46d7bbbc194f184f5c53
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470723B2
Reaction notes
Loading…