Potassium Carbonate → 1-(4-Ethynyl-2-methoxyphenyl)-4-methyl-1h-imidazole
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[N:11]1[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]1)[CH:6]=O.[C:17](=O)([O-])[O-].[K+].[K+].P(=O)([O-])OC(=[N+]=[N-])C(=O)C(C)C>CO>[C:6]([C:5]1[CH:8]=[CH:9][C:10]([N:11]2[CH:15]=[C:14]([CH3:16])[N:13]=[CH:12]2)=[C:3]([O:2][CH3:1])[CH:4]=1)#[CH:17]Participants
Procedure
3-Methoxy-4-(4-methyl-imidazol-1-yl)-benzaldehyde (2.00 g, 9.25 mmol) and anhydrous potassium carbonate (2.56 g, 18.5 mmol) were placed in a 250-mL flask and placed on high vacuum for 10 minutes. Under nitrogen, anhydrous MeOH (60 ml) was added via syringe. To the yellowish suspension was added dimethyl(1-diazo-2-oxopropyl) phosphonate (2.132 g, 11.10 mmol). The reaction was stirred at room temperature for 22 h. The reaction was quenched with aqueous sodium hydrogen carbonate (5%, 100 mL), and the mixture was diluted with diethyl ether (250 mL). The combined organic fractions were washed with brine (saturated, 2×100 mL), dried over MgSO4, filtered and evaporated. The residue was dried on high vacuum to give the title compound as a yellow solid (1.71 g, 87%). The product was pure enough by LCMS and NMR and not further purified.
Workup
- customThe reaction was quenched with aqueous sodium hydrogen carbonate (5%, 100 mL)
- additionthe mixture was diluted with diethyl ether (250 mL)
- washThe combined organic fractions were washed with brine (saturated, 2×100 mL)
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
- customThe residue was dried on high vacuum
Sources & evidence
- ORD record
- ord-b4617aeacaf8463abea507128ed30a14
- Source dataset
- uspto-grants-2012_08
- Patent number
- US08242150B2
Reaction notes
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