Potassium Iodide → ethyl (2-formyl-1H-imidazol-1-yl)acetate
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[I-].[K+]>C(#N)C>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH3:20]Participants
6
Conditions
- Temperature
- 50 °C
Procedure
To a solution of 1H-imidazole-2-carbaldehyde (4.47 g) in acetonitrile (80 ml) were added potassium carbonate (12.93 g), ethyl bromoacetate (6.2 ml) and potassium iodide (7.78 g) at room temperature. The mixture was stirred at 50° C. for 1 hour. After cooling to room temperature, the mixture was filtered to remove the precipitates. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography using dichloromethane and methanol (99:1 to 96:4) as eluents to afford the title compound (5.23 g, yield: 62%) as a brown oil.
Workup
- temperatureAfter cooling to room temperature
- filtrationthe mixture was filtered
- customto remove the precipitates
- concentrationThe filtrate was concentrated under reduced pressure
- customthe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-b132bd6183c54f3f8086dfcbf9e86ce4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07829580B2
Reaction notes
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