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Pyridine → Ethyl 2-isonicotinoyl-3-oxobutanoate

HRID 1011958
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1011958
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Cl-].[Mg+2].[Cl-].N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1>C(Cl)Cl>[CH2:8]([O:7][C:1](=[O:6])[CH:2]([C:19]([C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)=[O:26])[C:3](=[O:4])[CH3:5])[CH3:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8868Ethyl AcetoacetateHCID 417436Pyridine-4-carbonyl chlorideHCID 5360315Magnesium Chloride

Produkt 1

HCID 67314215Ethyl 2-isonicotinoyl-3-oxobutanoateAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

8 g (61.5 mmol) of ethyl acetoacetate were dissolved in 280 ml of CH2Cl2, the solution was cooled at 0° C. and successively were added 6.00 g (63.3 mmol) of anhydrous magnesium chloride, 10 ml (124 mmol) of pyridine and 13.4 g (94.73 mmol) of isonicotinoyl chloride. The yellow suspension was stirred 1 h under ice cooling and 18 h at room temperature. The reaction mixture was poured into crashed ice and extracted twice with CH2Cl2. The organic phases were washed with brine, dried over magnesium sulfate, and evaporated. The residue was purified by column chromatography (n-heptane:EtOAc 1:4) to afford the title compound as light yellow oil (6.75 g, 47%). MS: 236.0 (MH+).

Aufarbeitung

  1. additionThe reaction mixture was poured
  2. extractionextracted twice with CH2Cl2
  3. washThe organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by column chromatography (n-heptane:EtOAc 1:4)

Quellen und Nachweise

ORD-Eintrag
ord-afc972fc7b7a4294870cd409cba3560f
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07977358B2

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