Ethyl bromoacetate → Ethyl p-[5-(1-imidazolyl)pentyloxy]phenoxyacetate

HRID 329459Notes

Reaction equation

HRID 329459 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].[H-].[Na+]>CN(C)C=O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 132191404-{[5-(1H-Imidazol-1-yl)pentyl]oxy}phenol

Product 1

HCID 14327317Ethyl p-[5-(1-imidazolyl)pentyloxy]phenoxyacetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.46 g p-[5-(1-imidazolyl)pentyloxy]phenol and 1.2 ml ethyl bromoacetate in 25 ml anhydrous N,N-dimethylformamide, was added under ice cooling and with stirring 440 mg of 60% sodium hydride in oil, and stirring was continued at room temperature for ten minutes. The solvent was distilled off, the residue was dissolved in chloroform, and the solution was washed with water and dried over anhydrous sodium sulfate. After distilling off the chloroform, the residue was purified by silical gel column chromatography, affording 2.7 g of ethyl p-[5-(1-imidazol-yl)pentyloxy]phenoxyacetate as oil.

Workup

  1. waitwas continued at room temperature for ten minutes
  2. distillationThe solvent was distilled off
  3. dissolutionthe residue was dissolved in chloroform
  4. washthe solution was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationAfter distilling off the chloroform
  7. customthe residue was purified by silical gel column chromatography

Sources & evidence

ORD record
ord-0cf12de44d95418b8530a71dc0a31c93
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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