Water → Methyl 1-ethylindole-3-carboxylate
Reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1.[CH2:16](I)[CH3:17].O>CN(C=O)C>[CH2:16]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([O:14][CH3:15])=[O:13])=[CH:4]1)[CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In DMF (8.0 ml) was suspended sodium hydride (60% in oil, 273.9 mg, 6.846 mmol). To the resulting suspension was added methyl indole-3-carboxylate (399.8 mg, 2.282 mmol) under stirring at 0° C. The reaction mixture was stirred for 40 minutes at the same temperature. To the mixture was added ethyl iodide (0.27 ml, 3.423 mmol) at 0° C., followed by stirring at the same temperature for further 2 hours. Water was added to the reaction mixture to terminate the reaction. The reaction mixture was extracted with ethyl acetate. The extract was washed successively with 1N HCl and saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent, whereby methyl 1-ethylindole-3-carboxylate was obtained. The resulting compound was provided for the subsequent reaction without further purification.
Workup
- stirringThe reaction mixture was stirred for 40 minutes at the same temperature
- stirringby stirring at the same temperature for further 2 hours
- customto terminate
- customthe reaction
- extractionThe reaction mixture was extracted with ethyl acetate
- washThe extract was washed successively with 1N HCl and saturated brine
- dry with materialdried over anhydrous sodium sulfate
- distillationdistilled under reduced pressure
- customto remove the solvent
Sources & evidence
- ORD record
- ord-274ca016e4784038affc2b66edbd7365
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07157487B2
Reaction notes
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