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

HRID 2229126Notes

Reaction equation

HRID 2229126 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)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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c8fd647f8064429daae3de38fc4cf4c8
Source dataset
uspto-grants-2002_07
Patent number
US06420343B1

Reaction notes

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