Methyl iodide → 1-[5-(1-Imidazolyl)pentyloxy]-4-methoxybenzene

HRID 329460Notes

Reaction equation

HRID 329460 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.CI.[H-].[Na+].[C:23](OCC)(=O)C>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][CH3:23])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 132191404-{[5-(1H-Imidazol-1-yl)pentyl]oxy}phenol

Product 1

HCID 28435471-[5-(1-Imidazolyl)pentyloxy]-4-methoxybenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.87 g p-[5-(1-imidazolyl)pentyloxy]phenol and 0.46 ml methyl iodide in 18 ml anhydrous N,N-dimethylformamide, was added under ice cooling and with stirring 290 mg of 60% sodium hydride in oil, and stirring was continued at room temperature for five minutes. Ethyl acetate was added to the reaction mixture, the precipitate which separated out was filtered off, and the filtrate was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off, and the residue was purified by silica gel column chromatography [chloroform/methanol/28% ammonia water (50:1:0.1)], affording 2.0 g of 1-[5-(1-imidazolyl)pentyloxy]-4-methoxybenzene as oil.

Workup

  1. customthe precipitate which separated out
  2. filtrationwas filtered off
  3. washthe filtrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography [chloroform/methanol/28% ammonia water (50:1:0.1)]

Sources & evidence

ORD record
ord-b1f3a8db9cdf4bd982116f80f1d806fe
Source dataset
uspto-grants-1990_01
Patent number
US04891432

Reaction notes

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