Imidazole → 3-((Tert-butyldimethylsilyl)oxy)aniline

HRID 1675717Notes

Reaction equation

HRID 1675717 reaction equation
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[NH2:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.[Cl-].[Na+]>CN(C)C=O>[Si:6]([O:21][C:17]1[CH:16]=[C:15]([NH2:14])[CH:20]=[CH:19][CH:18]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 5234Sodium ChlorideHCID 115683-AminophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 143147823-((Tert-butyldimethylsilyl)oxy)anilineYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6.81 g (100 mmol) of imidazole and 9.04 g (60 mmol) of tert-butyl-dimethylsilyl chloride are added to a solution of 5.46 g (50 mmol) of 3-aminophenol in 13.5 ml of N,N-dimethylformamide. The resulting reaction mixture is stirred at room temperature for 12 h. After addition of a saturated aqueous sodium chloride solution, the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulphate. The crude product obtained after removal of the solvent by distillation is purified by flash chromatography. 7.62 g (34 mmol, 68%) of the desired product are obtained.

Workup

  1. customThe resulting reaction mixture
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulphate
  4. customThe crude product obtained
  5. customafter removal of the solvent
  6. distillationby distillation
  7. customis purified by flash chromatography

Sources & evidence

ORD record
ord-673b2d3ae5014d068fcf467cd13c7153
Source dataset
uspto-grants-2011_08
Patent number
US08003787B2

Reaction notes

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