Imidazole → 1-t-Butyldiphenylsiloxy-3,5-dimethoxybenzene

HRID 49283

Reaktionsgleichung

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.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].O>CN(C)C=O>[O:11]([C:5]1[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a solution of 3,5-dimethoxyphenol (6.73 g, 43.7 mmol) in anhydrous dimethylformamide (50 mL) were added imidazole (5.95 g, 87.4 mmol) and t-butylchlorodiphenylsilane (15.0 g, 54.6 mmol), and the mixture was stirred at 50° C. for 4 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate-hexane (1:2). The organic layer was washed with water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel to yield 1-t-butyldiphenylsiloxy-3,5-dimethoxybenzene as a colorless crystalline powder (melting point: 95.5-96.5° C.) (16.14 g, yield: 94%).

Aufarbeitung

extractionthe mixture was extracted with ethyl acetate-hexane (1:2)
washThe organic layer was washed with water
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-44d6565d2ae8422c8393a77b123d9947
Quelldatensatz: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06706703B2

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