Imidazole → tert-Butyl(3,5-dimethoxyphenoxy)dimethylsilane
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.CN(C=O)C.N1C=CN=C1.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>C(OCC)(=O)C.O>[C:22]([Si:26]([O:11][C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:29])[CH3:28])([CH3:25])([CH3:24])[CH3:23]Participants
Procedure
To a mixture of 3,5-dimethoxyphenol (3.00 g, 19.5 mmol) and DMF (45 mL) were added imidazole (2.66 g, 39.0 mmol) and tert-butyldimethylchlorosilane (2.94 g, 19.5 mmol) in that order, and the mixture was stirred for 19.5 hours at room temperature. Water was added to the reaction mixture, and then ethyl acetate was added. After thoroughly shaking the mixture, the organic layer was separated and the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The mixture was filtered, and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=9/1) to obtain the title compound (4.98 g, 18.6 mmol).
Workup
- stirringAfter thoroughly shaking the mixture
- customthe organic layer was separated
- washthe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe mixture was filtered
- distillationthe solvent in the filtrate was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography (mixture of n-heptane and ethyl acetate: n-heptane/ethyl acetate=9/1)
Sources & evidence
- ORD record
- ord-0681b199bf14445393ac25f63c75c44a
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431603B2
Reaction notes
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