Potassium Carbonate → YM 534

HRID 2165951Notes

Reaction equation

HRID 2165951 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.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:37])([CH3:36])[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(O)C>[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][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([CH3:36])([CH3:37])[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:16][CH:17]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 10444833Ethyl 6-bromo-2,2-dimethylhexanoateHCID 132191404-{[5-(1H-Imidazol-1-yl)pentyl]oxy}phenol

Product 1

HCID 130328YM 534

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

After 300 ml of ethanol was added to 35 g of p-[5-(1-imidazolyl)pentyloxy]phenol and 39 g of potassium carbonate, the mixture was heated at 60° C. with stirring and then cooled to room temperature. A solution of 43 g of ethyl 6-bromo-2,2-dimethylhexanoate in 50 ml of ethanol was added to the reaction mixture, and then the mixture was stirred under reflux overnight. The solvent was removed from the reaction mixture by distillation under reduced pressure and the residue was dissolved in chloroform. The solution was successively washed with a 1N aqueous sodium hydroxide solution, water, a saturated aqueous sodium chloride solution and then 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 a chloroform-methanol liquid mixture (30:1) as an eluant. The solvent was removed from the eluate by distillation. The residue was recrystallized from a mixture of ethyl acetate-n-hexane to give the desired product, ethyl 6-[p-[5-(1-imidazolyl)pentyloxy]phenoxy]-2,2-dimethylhexanoate.

Workup

  1. temperaturecooled to room temperature
  2. stirringthe mixture was stirred
  3. temperatureunder reflux overnight
  4. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
  5. dissolutionthe residue was dissolved in chloroform
  6. washThe solution was successively washed with a 1N aqueous sodium hydroxide solution, water
  7. dry with materiala saturated aqueous sodium chloride solution and then 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
  12. distillationeluate by distillation
  13. customThe residue was recrystallized from a mixture of ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-f176b2fba12744eab5702012dc06f04c
Source dataset
uspto-grants-1990_07
Patent number
US04942242

Reaction notes

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