Acetic Acid → 2-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde

HRID 432570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 432570
[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)(=O)C.[O:16]=[CH:17][C:18](=[CH2:20])[CH3:19]>C1COCC1>[CH3:19][CH:18]([CH2:20][N:10]1[CH:11]=[C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[N:8]=[CH:9]1)[CH:17]=[O:16]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 6562Methacrolein2×HCID 178420772HCID 178420772, Verbindung

Produkt 1

HCID 187597712-Methyl-3-(4-pyridin-3-yl-imidazol-1-yl)-propioaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-pyridin-3-yl-imidazole (8.5 g) in THF (293 mL) was added acetic acid (16.8 mL) and methacrolein (9.7 mL) and the resulting solution was heated under gentle reflux for 24 hours. Another 9.7 mL methacrolein was added and the solution was heated under reflux for another 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 long column eluting with MeOH—CH2Cl2 to give the title compound as slightly yellow oil.

Aufarbeitung

  1. temperaturethe resulting solution was heated
  2. temperatureunder gentle reflux for 24 hours
  3. temperaturethe solution was heated
  4. temperatureunder reflux for another 24 hours
  5. customTHF was then removed in vacuo
  6. customthe residue was purified on a Flash 75 long column
  7. washeluting with MeOH—CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-4d2c8b545199473fad18556ba2df287a
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06664238B1

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