Ethyl Propionate → 1-(3-Pyridyl)propan-1-one

HRID 359321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 359321
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[C:12](OCC)(=O)[CH2:13]C.[O-]CC.[Na+]>O>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([CH2:12][CH3:13])=[O:9])[CH:3]=1

Komponenten

5

Edukt 3

HCID 7749Ethyl PropionateHCID 69188Ethyl NicotinateHCID 2723922Sodium ethoxide

Produkt 1

HCID 740741-(3-Pyridyl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of ethyl nicotinate (15.1 g, 0.1 mole), ethyl propionate (15.3 g, 0.15 mole) and sodium ethoxide (10.2 g, 0.15 mole) was stirred and heated under nitrogen at 100°C. for five hours. After cooling, the mixture was diluted with water (150 ml) extracted with diethyl ether (50 ml) and the aqueous layer made acidic to pH 1 with concentrated hydrochloric acid (50 ml). The aqueous layer was heated at 90°C. for two hours, cooled, made alkaline with solid potassium carbonate and extracted with diethyl ether (3×75 ml). The dried (magnesium sulphate) organic layer was concentrated and distilled to give ethyl 3-pyridyl ketone (b.pt 97-99°/14mm Hg).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether (50 ml)
  3. temperatureThe aqueous layer was heated at 90°C. for two hours
  4. temperaturecooled
  5. extractionextracted with diethyl ether (3×75 ml)
  6. dry with materialThe dried (magnesium sulphate) organic layer
  7. concentrationwas concentrated
  8. distillationdistilled

Quellen und Nachweise

ORD-Eintrag
ord-78d4eb6ec89e452f868b2ce90a32fba4
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US05000946

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