3-Ethoxy-4-fluorobenzaldehyde → 3-ethoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde
Reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1F)[CH:13]=[O:14])[CH3:8]>CN(C=O)C>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[N:5]1[CH:6]=[C:2]([CH3:1])[N:3]=[CH:4]1)[CH:13]=[O:14])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
4-methylimidazole (244 mg) was added to a DMF (3 mL) solution of 3-ethoxy-4-fluorobenzaldehyde (250 mg) obtained above, and the reaction solution was agitated at 150° C. for 4 hours. The reaction solution was concentrated as it was after the reaction ended, water and ethyl acetate were added to the obtained reaction residue, and the organic layer was separated. The obtained organic layer was washed with a saturated sodium chloride solution, and the solvent was evaporated under reduced pressure after dried over anhydrous magnesium sulfate. The obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 1:4), and 60 mg (18%) of 3-ethoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde was obtained. The physical properties of the compound are as follows.
Workup
- customobtained above, and the reaction solution
- concentrationThe reaction solution was concentrated as it
- additionwater and ethyl acetate were added to the obtained reaction residue
- customthe organic layer was separated
- washThe obtained organic layer was washed with a saturated sodium chloride solution
- customthe solvent was evaporated under reduced pressure
- dry with materialafter dried over anhydrous magnesium sulfate
- customThe obtained residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate 1:4)
Sources & evidence
- ORD record
- ord-fe5ac0a775a84531be4c3b2d8b4fe792
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07880009B2
Reaction notes
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