Ethanol → β-Methyl-4-(3-pyridinyl)-1H-imidazole-1-propanal

HRID 2229126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2229126
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[CH:9][NH:10][CH:11]=2)[CH:2]=1.C(O)C.[CH:15](=[O:19])/[CH:16]=[CH:17]/[CH3:18]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:8]=[CH:9][N:10]([CH:17]([CH3:18])[CH2:16][CH:15]=[O:19])[CH:11]=2)[CH:2]=1

Komponenten

5

Edukt 3

HCID 702EthanolHCID 447466Crotonaldehyde2×HCID 178420772HCID 178420772, Verbindung

Produkt 1

HCID 18759767β-Methyl-4-(3-pyridinyl)-1H-imidazole-1-propanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution 4pyridin-3-yl-imidazole (10 g, 68.88 mmol) in THF (300 ml) were added ethanol (4.04 ml, 68.88 mmol) and crotonaldehyde (22.83 ml, 275.52 mmol). The resulting mixture was heated under reflux for 18 hours. At this point of time, an additional 2 equiv of crotonaldehyde was added and contiuned to reflux for another 20 hours. TLC analysis indicated the reaction was complete. Solvent was removed in vacuo and the crude aldehyde of formula 18, wherein R7 is methyl and R3 is pyridin-3-yl, which was used without purification.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperatureto reflux for another 20 hours
  4. customSolvent was removed in vacuo
  5. customthe crude aldehyde of formula 18, wherein R7 is methyl and R3 is pyridin-3-yl, which was used without purification

Quellen und Nachweise

ORD-Eintrag
ord-c8fd647f8064429daae3de38fc4cf4c8
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420343B1

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