Ethyl Acetate → 3-Oxo-2-(pyridin-3-yl)butanenitrile

HRID 75507

Reaktionsgleichung

Reaktionsgleichung von HRID 75507
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1.[H-].[Na+].[CH3:12][CH2:13][O:14]C(C)=O>C1COCC1>[O:14]=[C:13]([CH3:12])[CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:8]#[N:9]

Komponenten

5

Edukt 3

HCID 8857Ethyl Acetate2×HCID 24758Sodium hydrideHCID 809233-Pyridineacetonitrile

Produkt 1

HCID 673626493-Oxo-2-(pyridin-3-yl)butanenitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2-(Pyridin-3-yl)acetonitrile (7.00 g, 59.3 mmol) was dissolved in THF (100 ml). NaH (60% in oil) (5.93 g, 148 mmol) was slowly added and the reaction mixture was stirred at RT for 1 hour (continuous gentle gas evolution). EtOAc (1 ml) was added and the mixture was stirred until an exothermic reaction occurred. EtOAc (7 mL) was then added slowly to maintain gentle heating. The reaction was stirred at RT for 2 hours and then approximately 75% of the THF was removed in vacuo. The resulting mixture was partitioned between Et2O and water and the aqueous phase was washed with Et2O (2×50 mL). The aqueous phase was then acidified with 1M HCl and the product was extracted into EtOAc. A significant amount of solid gradually formed between the two layers. This material was filtered off and dried.

Aufarbeitung

  1. stirringthe mixture was stirred until an exothermic reaction
  2. temperatureto maintain gentle heating
  3. stirringThe reaction was stirred at RT for 2 hours
  4. customapproximately 75% of the THF was removed in vacuo
  5. customThe resulting mixture was partitioned between Et2O and water
  6. washthe aqueous phase was washed with Et2O (2×50 mL)
  7. extractionthe product was extracted into EtOAc
  8. customA significant amount of solid gradually formed between the two layers
  9. filtrationThis material was filtered off
  10. customdried

Quellen und Nachweise

ORD-Eintrag
ord-3f58cba89873466883fe0c34f5a1eb50
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835444B2

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