Imidazole → 6-((tert-butyldimethylsilyl)oxy)-1H-indole

HRID 1726102Notes

Reaction equation

HRID 1726102 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C)C=O.C(OCC)(=O)C>[Si:11]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5245086-Hydroxyindole

Product 1

HCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indoleYield 99.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.52 g of 6-hydroxyindole, 4.78 g of tert-butyldimethylsilyl chloride, and 4.5 g of imidazole in 16 ml of dimethylformamide is stirred at ambient temperature overnight. The reaction medium is diluted with ethyl acetate and the organic phase is then washed with 2 times 50 ml of distilled water. The organic phase is dried over magnesium sulfate and filtered, and the solvent is evaporated off in a rotary evaporator to obtain 6.5 g of 6-(tert-butyl-dimethylsilanyloxy)-1H-indole.

Workup

  1. washthe organic phase is then washed with 2 times 50 ml of distilled water
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent is evaporated off in a rotary evaporator

Sources & evidence

ORD record
ord-831407fac42c4838b8841ae8b44140c7
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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