Potassium Carbonate → HCID 14349179, compound

HRID 414725Notes

Reaction equation

HRID 414725 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C(=O)([O-])[O-].[K+].[K+].Br[C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(O)C>[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([O:12][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 823151-(p-Hydroxyphenyl)imidazole

Product 1

HCID 14349179HCID 14349179, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 50 ml of ethanol was dissolved 1.6 g of p-(1-imidazolyl)phenol and 1.4 g of anhydrous potassium carbonate was added to the solution. While stirring, 2.1 g of ethyl α-bromoisobutyrate was dropwise added to the mixture. Thereafter stirring was continued for 20 hours under reflux. After cooling to room temperature, the solvent was removed from the reaction mixture in vacuo. The residue was dissolved in methylene chloride. After the solution was successively washed with a 5% aqueous hydrogen sodium carbonate solution, water and a saturated aqueous sodium chloride solution, the solution was dried over anhydrous sodium sulfate. After drying, the solvent was removed by distillation under reduced pressure and the residue was subjected to silica gel column chromatography. The product was eluted out using chloroform-methanol (9:1) as an eluant. The solvent was removed from the eluate under reduced pressure to give the desired product, ethyl 2-[p-(1-imidazolyl)phenoxy]-2-methylpropionate, as an oily substance.

Workup

  1. additionwas added to the solution
  2. stirringThereafter stirring
  3. temperatureunder reflux
  4. customthe solvent was removed from the reaction mixture in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. washAfter the solution was successively washed with a 5% aqueous hydrogen sodium carbonate solution, water
  7. dry with materiala saturated aqueous sodium chloride solution, the solution was dried over anhydrous sodium sulfate
  8. customAfter drying
  9. customthe solvent was removed by distillation under reduced pressure
  10. washThe product was eluted out
  11. customThe solvent was removed from the eluate under reduced pressure

Sources & evidence

ORD record
ord-7425a12d477e44748375d8dc1f1b0eb8
Source dataset
uspto-grants-1988_12
Patent number
US04794113

Reaction notes

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