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

HRID 751195

Reaktionsgleichung

Reaktionsgleichung von HRID 751195
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.C(OCC)C>CN(C=O)C>[C:14]([Si:11]([CH3:13])([CH3:12])[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([CH3:17])([CH3:16])[CH3:15]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 160545-HydroxyindoleHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 5-hydroxy-indole (5 g, 38 mmol), tert-butyldimethylsilyl chloride (6.13 g, 39.4 mmol) and imidazole (5.37 g, 68.1 mmol) in DMF (50 ml) was stirred for 20 h at RT. Diethyl ether was added and the mixture was washed with 1N HCl and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 9.4 g (38 mmol, quant.) 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole.

Aufarbeitung

  1. washthe mixture was washed with 1N HCl and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3f63406704fd44c7a2243ee88acf4a89
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405236B2

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