Imidazole → 4-(t-Butyldimethylsilyloxy)indole

HRID 1601464Notes

Reaction equation

HRID 1601464 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.[Cl-].[NH4+]>CN(C)C=O>[Si:11]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 754211H-indol-4-ol

Product 1

HCID 115939764-(t-Butyldimethylsilyloxy)indoleYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-hydroxyindole (3.0 g, 22.5 mmol), t-butyldimethylsilyl chloride (5.09 g, 33.8 mmol) and imidazole (3.83 g, 56.3 mmol) in dimethylformamide (60 mL) was stirred at room temperature for 24 hours. Aqueous ammonium chloride was added (100 ml) and extracted several times with ethyl acetate. The organic layers were combined, dried over magnesium sulfate, and evaporated to give a crude oil. Flash chromatography (10% ethyl acetate/hexanes) yielded the desired product (5.55 g, 100%) as a white solid. NMR.

Workup

  1. extractionextracted several times with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a crude oil

Sources & evidence

ORD record
ord-ffc50030f61148a59cb513adcfa71055
Source dataset
uspto-grants-1999_11
Patent number
US05977154

Reaction notes

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