Dimethylformamide → Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylate

HRID 1359680Notes

Reaction equation

HRID 1359680 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9]([C:11]1[NH:12][CH:13]=[C:14]([CH3:16])[CH:15]=1)=[O:10])[CH3:7].[OH-].[Na+].CN(C)[CH:21]=[O:22]>O>[CH2:6]([O:8][C:9]([C:11]1[NH:12][C:13]([CH:21]=[O:22])=[C:14]([CH3:16])[CH:15]=1)=[O:10])[CH3:7]

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 643361Ethyl 4-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 9855648Ethyl 5-formyl-4-methyl-1H-pyrrole-2-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the ice-cold solution of dimethylformamide (DMF) (3 mL, 39.2 mmol) was added phosphorus oxychloride (0.67 mL, 7.18 mmol) dropwise and the resultant mixture was stirred for 30 minutes. A solution of (1 g, 6.53 mmol) of 4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester in 3 mL of DMF was added to the reaction. After 1 h, the reaction was warmed to room temperature for another 2.5 h. The reaction mixture was diluted with water (100 mL) and basified to pH=11 with 1N sodium hydroxide solution. The precipitate was removed by filtration, rinsing with water and dried to afford 0.8 g (68%) of 5-formyl-4-methyl-1H-pyrrole-2-carboxylic acid ethyl ester as a white solid.

Workup

  1. customThe precipitate was removed by filtration
  2. washrinsing with water
  3. customdried

Sources & evidence

ORD record
ord-5a0173299b8a49adabbbb35f3e2f5b3f
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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