[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]
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).
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