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

HRID 751195

Reaction equation

HRID 751195 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3f63406704fd44c7a2243ee88acf4a89
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Linked notes

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