Iodoethane → 1-ethyl-1H-imidazole-2-carbaldehyde
Reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7].C(=O)([O-])[O-].[K+].[K+].I[CH2:15][CH3:16]>CN(C)C=O>[CH2:15]([N:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=[O:7])[CH3:16]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a suspension of 1H-imidazole-2-carbaldehyde (480 mg, 5 mmol) and potassium carbonate (936 mg, 6 mmol) in N,N-dimethylformamide (7 mL) was added iodoethane (829 mg, 6 mmol) and the mixture was heated at 50° C. for 5 hrs. Solvent was removed under reduced pressure. The residue was partitioned between water (30 mL) and ethyl acetate (30 mL). The aqueous layer was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give 1-ethyl-1H-imidazole-2-carbaldehyde as light yellow oil (520 mg, yield 84%). 1H NMR (400 MHz, CDCl3) δ (ppm): 1.42-1.46 (t, J=7.2 Hz, 3H), 4.42-4.47 (q, 2H), 7.19 (s, 1H), 7.29 (s, 1H), 9.82 (s, 1H). LC-MS (ESI) m/z: 125 (M+1)+.
Workup
- customSolvent was removed under reduced pressure
- customThe residue was partitioned between water (30 mL) and ethyl acetate (30 mL)
- extractionThe aqueous layer was extracted with ethyl acetate (20 mL×3)
- washThe combined organic layers were washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b991f40bab314c948700a07c0ba92eb6
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420650B2
Reaction notes
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