Potassium Carbonate → Methyl [(2-cyanopyridin-3-yl)oxy]acetate

HRID 2109058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2109058
[C:1]([C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].Br[CH2:11][C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1[C:8]([O:9][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 1019203-Hydroxypyridine-2-carbonitrile

Produkt 1

HCID 57633316Methyl [(2-cyanopyridin-3-yl)oxy]acetateAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-Cyano-3-hydroxypyridine (5.00 g) is dissolved in acetone (50 ml), and thereto are added methyl bromoacetate (7.0 g) and potassium carbonate (6.3 g). The mixture is heated under reflux for 1.5 hours. After allowing to cool, ice-water is poured to the reaction solution and extracted with ethyl acetate. The organic layer is washed with saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended in diethyl ether/n-hexane and the solid is collected by filtration to give the title compound (7.91 g).

Aufarbeitung

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 1.5 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe organic layer is washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. filtrationthe solid is collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-626e3a24cef343b0b01c208e09b1afa6
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07514449B2

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