Tetrahydrofuran → 1-(5-Methylpyridin-3-yl)ethan-1-one

HRID 2195723

Reaktionsgleichung

Reaktionsgleichung von HRID 2195723
[CH3:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)C#N.[C:10]([O-:13])([O-])=O.[Na+].[Na+].[CH2:16]1COCC1>CCOCC>[CH3:1][C:2]1[CH:9]=[C:6]([C:10](=[O:13])[CH3:16])[CH:5]=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 6378385-Methylnicotinonitrile

Produkt 1

HCID 5775691-(5-Methylpyridin-3-yl)ethan-1-oneAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

5-Methyl-nicotinonitrile (2.08 g, 17.6 mmol) is heated at reflux in dry THF (20 mL) with MgMeBr (3 M solution in Et2O, 10 mL, 30 mmol) for 2 h. After cooling down, aq. Na2CO3 is added slowly to quench the reaction. Extractions with DCM affords the crude mixture which is purified by silica gel chromatography to yield 1-(5-methyl-pyridin-3-yl)-ethanone 18 (0.7 g, 30%). LC/MS (m/z) (M+1)+: 136.1.

Aufarbeitung

  1. temperatureAfter cooling down
  2. customto quench
  3. customthe reaction
  4. extractionExtractions with DCM
  5. customaffords the crude mixture which
  6. customis purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3512003bfe85409fb343489eb337bf82
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338417B2

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