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

HRID 432566Notes

Reaction equation

HRID 432566 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 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 long column
  5. washeluting with MeOH—CH2Cl2

Sources & evidence

ORD record
ord-99af1a7f242247738838944abf1c9361
Source dataset
uspto-grants-2003_12
Patent number
US06664238B1

Reaction notes

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