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

HRID 432565Notes

Reaction equation

HRID 432565 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.[O:16]=[CH:17][C:18](=[CH2:20])[CH3:19]>O1CCCC1>[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]

Participants

5

Reactant 3

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

Product 1

HCID 187597712-Methyl-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 (8.5 g) in THF (tetrahydrofuran) (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.

Workup

  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

Sources & evidence

ORD record
ord-dd026eb52848401abf529341a002f90a
Source dataset
uspto-grants-2003_12
Patent number
US06664238B1

Reaction notes

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