Reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH3:15])=[CH:12][C:6]([CH2:7][O:8][CH2:9][CH:10]=[CH2:11])=[C:5]([N+:16]([O-:18])=[O:17])[CH:4]=1.[CH3:19][O:20][SiH:21]([O:24][CH3:25])[O:22][CH3:23]>[H+].[H+].O.O.O.O.O.O.Cl[Pt-2](Cl)(Cl)(Cl)(Cl)Cl>[CH3:19][O:20][Si:21]([O:24][CH3:25])([O:22][CH3:23])[CH2:11][CH2:10][CH2:9][O:8][CH2:7][C:6]1[CH:12]=[C:13]([O:14][CH3:15])[C:3]([O:2][CH3:1])=[CH:4][C:5]=1[N+:16]([O-:18])=[O:17]Participants
Conditions
- Temperature
- 37 °C
Procedure
A 30-ml eggplant type flask was purged with nitrogen, and charged with 1.5 g (5.9 mmol) of allyl 4,5-dimethoxy-2-nitrobenzyl ether, 0.865 g (7.1 mmol) of trimethoxysilane, and an infinitesimal amount of hydrogen hexachloroplatinate(IV) hexahydrate (H2PtCl6·6H2O), followed by stirring at 37° C. for 30 minutes. Thereafter, the bath temperature was raised to 100° C., and the reaction was completed in 2 hours. The reaction mixture was purified by silica gel column chromatography using a medium-pressure column. Using a mixture of hexane, ethyl acetate and tetramethoxysilane (in a volume ratio of 100:20:1) as the eluent, 0.95 g (2.53 mmol) of the desired product was obtained in a 43% yield. Its Rf value (for the aforesaid eluent) was 0.19.
Workup
- customA 30-ml eggplant type flask was purged with nitrogen
- temperatureThereafter, the bath temperature was raised to 100° C.
- waitthe reaction was completed in 2 hours
- customThe reaction mixture was purified by silica gel column chromatography
- additiona mixture of hexane, ethyl acetate and tetramethoxysilane (in a volume ratio of 100:20:1) as the eluent
Sources & evidence
- ORD record
- ord-2e3373ca8d82480594f14dbad63462c3
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07112397B2
Linked notes
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