Imidazole → Ethyl 2-[o-(1-imidazolylmethyl)phenoxy]propionate

HRID 1249544Notes

Reaction equation

HRID 1249544 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Br[CH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[O:12][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>CN(C)C=O>[NH:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH2:9][C:10]1[CH:23]=[CH:22][CH:21]=[CH:20][C:11]=1[O:12][CH:13]([CH3:19])[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 11808300Ethyl 2-(2-bromomethylphenoxy)propionate

Product 1

HCID 70455782Ethyl 2-[o-(1-imidazolylmethyl)phenoxy]propionateYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5.7 g of 50% sodium hydride in 200 ml of dry dimethylformamide was added slowly 8.0 g of imidazole at room temperature, and then the mixture was stirred for 30 minutes. A solution of 34.1 g of ethyl 2-(o-bromomethylphenoxy)propionate in 50 ml of dry dimethylformamide was added to the mixture at room temperature over a period of 1 hour, and then the reaction mixture was stirred at the same temperature for 1 hour. After removal of the solvent under vacuum, 150 ml of dichloromethane was added to the residual oil and the solution was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residual oil was chromatographed on silica gel using dichloromethane-ethanol (20:1 by volume) to give 15 g of ethyl 2-[o-(1-imidazolylmethyl)phenoxy]propionate as colorless needles. M.P.: 84°-85° C.

Workup

  1. stirringthe reaction mixture was stirred at the same temperature for 1 hour
  2. customAfter removal of the solvent under vacuum, 150 ml of dichloromethane
  3. additionwas added to the residual oil
  4. washthe solution was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residual oil was chromatographed on silica gel

Sources & evidence

ORD record
ord-e77e5f92849e402b966c66d1c459176f
Source dataset
uspto-grants-1986_12
Patent number
US04632934

Reaction notes

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