Potassium Carbonate → YM 534

HRID 414726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 414726
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 130328YM 534

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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 over 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.

Aufarbeitung

  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 over 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

Quellen und Nachweise

ORD-Eintrag
ord-b5c7b66a6e784ee6bdf1c2e2bdf4d7c9
Quelldatensatz
uspto-grants-1988_12
Patentnummer
US04794113

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