Dimethylformamide → ethyl 5-formyl-1,4-dimethyl-1H-pyrrole-2-carboxylate

HRID 1662046Notes

Reaction equation

HRID 1662046 reaction equation
[CH:1]([C:3]1[NH:7][C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][C:4]=1[CH3:13])=[O:2].[CH3:14]N(C=O)C.[H-].[Na+].CI>O>[CH:1]([C:3]1[N:7]([CH3:14])[C:6]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:5][C:4]=1[CH3:13])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 9855648Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 59454108ethyl 5-formyl-1,4-dimethyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate (0.97 g) and DMF (10 ml) was added sodium hydride (0.23 g) under ice-cooling, followed by stirring at room temperature for 0.5 hour. To a reaction mixture was added methyl iodide under ice-cooling, followed by stirring at room temperature for 15 hours. To the reaction mixture was added water under ice-cooling, followed by stirring at room temperature. The solid precipitated was collected by filtration and washed with water to obtain ethyl 5-formyl-1,4-dimethyl-1H-pyrrole-2-carboxylate (1.0 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringby stirring at room temperature for 15 hours
  4. temperaturecooling
  5. stirringby stirring at room temperature
  6. customThe solid precipitated
  7. filtrationwas collected by filtration
  8. washwashed with water

Sources & evidence

ORD record
ord-f45950a30d04439ba68e8bc1a61351d6
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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