Hydrochloric Acid → t-Butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[O:10][CH3:11].N1C=CN=C1.[C:17]([Si:21](Cl)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([CH3:20])([CH3:19])[CH3:18].Cl>CN(C=O)C.C(OCC)(=O)C>[C:17]([Si:21]([O:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([O:10][CH3:11])[CH:4]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([CH3:20])([CH3:18])[CH3:19]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
After dissolving 9.17 g of (4-fluoro-3-methoxyphenyl)methanol [CAS No. 128495-45-4] in 100 ml of DMF, 5 g of imidazole and 17 g of t-butyl-chlorodiphenylsilane were added and the mixture was stirred overnight at room temperature. Next, 1N hydrochloric acid was added to the reaction mixture, and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was filtered off and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give t-butyl-(4-fluoro-3-methoxybenzyloxy)diphenylsilane as an oil.
Workup
- dry with materialThe organic layer was dried over anhydrous magnesium sulfate
- filtrationThe desiccating agent was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)
Sources & evidence
- ORD record
- ord-6eda95eb6c8141afb5edc10f053c762a
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08163787B2
Reaction notes
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