Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

HRID 20984

Reaktionsgleichung

Reaktionsgleichung von HRID 20984
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].C(=O)([O-])O.[Na+]>CN(C=O)C>[Si:16]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 160545-HydroxyindoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indoleAusbeute 133,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Hydroxyindole (209 mg, 1.57 mmol) was dissolved in DMF (6 mL), and the solution was added with imidazole (132 mg, 1.93 mmol) and tert-butyldimethylsilyl chloride (333 mg, 2.21 mmol) at 0° C. followed by stirring at room temperature for 3.5 hours. The reaction mixture was added with saturated aqueous sodium hydrogencarbonate solution at 0° C. and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 5-(tert-butyldimethylsilyloxy)indole (517 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1f3d8217c1964a0ebeb2119a90db494a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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