3-Hydroxybenzaldehyde → 3-(t-Butyldimethylsilyloxy)benzaldehyde

HRID 350839

Reaktionsgleichung

Reaktionsgleichung von HRID 350839
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17].C(OCC)(=O)C>C(#N)C>[Si:20]([O:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:23])[CH3:22]

Komponenten

6

Edukt 4

HCID 1013-HydroxybenzaldehydeHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 112071113-(t-Butyldimethylsilyloxy)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Hydroxybenzaldehyde (5.0 g, 40.9 mmol) was dissolved in acetonitrile (10.0 mL). Subsequently, potassium carbonate (11.3 g, 81.9 mmol), and then tert-butyldimethylchlorosilane (7.4 g, 49.1 mmol) were added thereto, and the resultant mixture was stirred at room temperature. After completion of reaction, ethyl acetate was added thereto, followed by washing sequentially with water and brine, and drying over anhydrous sodium sulfate. The reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound was obtained (9.1 g, 94%).

Aufarbeitung

  1. additionwas added
  2. washby washing sequentially with water and brine
  3. dry with materialdrying over anhydrous sodium sulfate
  4. filtrationThe reaction mixture was subjected to filtration, concentration under reduced pressure, and purification by silica gel column chromatography (n-hexane/ethyl acetate=20/1), whereby the target compound
  5. customwas obtained (9.1 g, 94%)

Quellen und Nachweise

ORD-Eintrag
ord-bf7cce1f6f964bab81c4ef86d74f3c34
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183295B2

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