Water → 1-(5-Carboxy-2-pyridinyl)-1-butanone

HRID 1200031Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1200031
[CH2:1]([Mg]Br)[CH2:2][CH3:3].[C:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15]#N)=[N:13][CH:14]=1)([OH:8])=[O:7].O.[OH:18]S(O)(=O)=O>CCOCC.O1CCCC1>[C:6]([C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:18])[CH2:1][CH2:2][CH3:3])=[N:13][CH:14]=1)([OH:8])=[O:7]

Komponenten

7

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 27611086-Cyanopyridine-3-carboxylic acidHCID 178455851HCID 178455851, Verbindung

Produkt 1

HCID 198645601-(5-Carboxy-2-pyridinyl)-1-butanone

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of propyl magnesium bromide (67.5 mmol) in 80 ml of ether, 5-carboxy-2-cyano-pyridine (30.7 mmol), dissolved in 100 ml of tetrahydrofuran, is added dropwise. The mixture is refluxed for 20 h. After cooling, 10 ml of water and 5 ml of 5N H2SO4 are added. Extraction of the aqueous phase with ether and evaporation of the solvent yield 3.5 g of crude product. Purification by silica gel column chromatography (n-hexane: ethyl acetate: HCOOH 7:3:0.1) yields the title compound, m.p. 128°-130°.

Aufarbeitung

  1. additionis added dropwise
  2. temperatureThe mixture is refluxed for 20 h
  3. temperatureAfter cooling
  4. extractionExtraction of the aqueous phase
  5. customwith ether and evaporation of the solvent yield 3.5 g of crude product
  6. customPurification by silica gel column chromatography (n-hexane: ethyl acetate: HCOOH 7:3:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-3501d9a67bcb410b91e87632accfc0b0
Quelldatensatz
uspto-grants-1990_02
Patentnummer
US04904675

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