Acetic Acid → 3,3-Dimethyl-3(4-Pyridin-3-yl-imidazol-1-yl)-propioaldehyde

HRID 2229127Notes

Reaction equation

HRID 2229127 reaction equation
[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.[CH3:16][C:17]([CH3:21])=[CH:18][CH:19]=[O:20]>C1COCC1>[CH3:16][C:17]([CH3:21])([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)[CH2:18][CH:19]=[O:20]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 610203-Methyl-2-butenalHCID 178420772HCID 178420772, compound

Product 1

HCID 114816033,3-Dimethyl-3(4-Pyridin-3-yl-imidazol-1-yl)-propioaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-pyridin-3-yl-imidazole (1 g) in THF (34 mL) was added acetic acid (1.6 mL) and 3-methyl-2-butenal (3.3 mL) and the resulting solution was heated under gentle reflux for 24 hours. THF was then removed in vacuo and the residue was purified on a Flash 75 (silica gel column made by Biotage Division of Dyax Corp, U.S.) long column eluting with MeOH—CH2Cl2 to give the title compound as slightly yellow oil.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder gentle reflux for 24 hours
  3. customTHF was then removed in vacuo
  4. customthe residue was purified on a Flash 75 (silica gel column made by Biotage Division of Dyax Corp, U.S.) long column
  5. washeluting with MeOH—CH2Cl2

Sources & evidence

ORD record
ord-2afb7614fdc44a1694030b646f2fd78c
Source dataset
uspto-grants-2002_07
Patent number
US06420343B1

Reaction notes

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