Methyl iodide → Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

HRID 515864

Reaction equation

HRID 515864 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

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136747Ethyl 2-methyl-3-pyrrolecarboxylate

Product 1

HCID 12211514Ethyl 1,2-dimethyl-1H-pyrrole-3-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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 (NaH) 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 aqueous hydrochloric acid (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

  1. customplaced at 0° C.
  2. washsuccessively washed with 0.1M aqueous hydrochloric acid (HCl) solution, saturated aqueous LiCl solution
  3. dry with materialThe organic phase is then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. custompurified by chromatography over silica gel (petroleum ether/AcOEt gradient)

Sources & evidence

ORD record
ord-527b8670a95e40e989aab6cfe6fb9720
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Linked notes

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