Imidazole → 1-(5-{[Tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)ethanone

HRID 1888717

Reaktionsgleichung

Reaktionsgleichung von HRID 1888717
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1.[C:14]([Si:18]([CH3:21])([CH3:20])Cl)([CH3:17])([CH3:16])[CH3:15].N1C=CN=C1>CN(C=O)C.[Cl-].[Na+].O>[Si:18]([O:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10](=[O:12])[CH3:11])=[CH:7][C:6]=2[CH:13]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:21])[CH3:20]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 32378771-(5-Hydroxy-1-benzofuran-2-yl)ethanone

Produkt 1

HCID 580474981-(5-{[Tert-butyl(dimethyl)silyl]oxy}-1-benzofuran-2-yl)ethanoneAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a solution of 1-(5-hydroxy-1-benzofuran-2-yl)ethanone (1.15 g, 6.53 mmol) in DMF (10 mL) were added tert-butyldimethylchlorosilane (1.07 g, 7.18 mmol) and imidazole (666 mg, 9.80 mmol), and the mixture was stirred at room temperature overnight. To the reaction mixture was added brine, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 7:3) to give the title compound (1.76 g, yield 98%).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 7:3)

Quellen und Nachweise

ORD-Eintrag
ord-e75679760d1d4a34b75322d4fa669360
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501804B2

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