Methyl iodide → Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate
Reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH3:12]I.[H-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:12][N:3]1[CH:4]=[CH:5][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]1[CH3:1]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 10 g of ethyl 2-methyl-1H-pyrrole-3-carboxylate (65.3 mmol) and 8.95 mL (130.6 mmol) of methyl iodide in 70 mL of dimethylformamide placed at 0° C. there are added, in three portions, 2.61 g (65.3 mmol) of sodium hydride 60%. The batch is then stirred at 0° C. for 1 hour. Then, the reaction mixture is hydrolysed by the addition of 420 mL of ice-cold water. The reaction mixture is then diluted with ethyl acetate, successively washed with 0.1M HCl solution, saturated aqueous LiCl solution and then brine. The organic phase is then dried over MgSO4, filtered, concentrated to dryness and purified by chromatography over silica gel (petroleum ether/AcOEt gradient).
Workup
- customplaced at 0° C.
- washsuccessively washed with 0.1M HCl solution, saturated aqueous LiCl solution
- dry with materialThe organic phase is then dried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness
- custompurified by chromatography over silica gel (petroleum ether/AcOEt gradient)
Sources & evidence
- ORD record
- ord-2b85008782ed40f69d0258f7944edc6f
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115159B2
Reaction notes
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