Dimethylformamide → Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylate

HRID 1107813Notes

Reaction equation

HRID 1107813 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][C:7]1[CH:8]=[C:9]([C:13]([O:15][CH3:16])=[O:14])[NH:10][C:11]=1[CH3:12].CN(C)[CH:19]=[O:20].[OH-].[Na+]>>[CH:19]([C:8]1[C:7]([CH3:6])=[C:11]([CH3:12])[NH:10][C:9]=1[C:13]([O:15][CH3:16])=[O:14])=[O:20]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 22719654HCID 22719654, compound

Product 1

HCID 10773740Methyl 3-formyl-4,5-dimethyl-1H-pyrrole-2-carboxylateYield 64.9%

Procedure

15.0 g (0.0979 mole) of phosphorus oxychloride were dropwise added to a solution of 13.7 g (0.0898 mole) of methyl 4,5-dimethylpyrrole-2-carboxylate in 13 ml (0.17 mole) of dimethylformamide over a period of 1.3 hours with ice-cooling, and the resulting mixture was stirred at room temperature for 0.5 hour and then at 90-100° C. for 0.5 hour. The hot reaction mixture thus obtained was poured into ice-water and dissolved. The solution was adjusted to pH 5-6 with a 10% aqueous solution of sodium hydroxide. The solids precipitated were collected by filtration and then dissolved in 600 ml of ethyl acetate. The filtrate was extracted twice with 200 ml each of ethyl acetate. The combined extracts were washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off. The residue was washed with a mixture of hexane and ethyl acetate and collected by filtration to give 10.6 g (0.0583 mole) of methyl 3-formyl-4,5-dimethylpyrrole-2-carboxylate as a brown powder.

Workup

  1. temperaturecooling
  2. waitat 90-100° C. for 0.5 hour
  3. customThe hot reaction mixture thus obtained
  4. dissolutiondissolved
  5. customThe solids precipitated
  6. filtrationwere collected by filtration
  7. dissolutiondissolved in 600 ml of ethyl acetate
  8. extractionThe filtrate was extracted twice with 200 ml each of ethyl acetate
  9. washThe combined extracts were washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off
  12. washThe residue was washed with a mixture of hexane and ethyl acetate
  13. filtrationcollected by filtration

Sources & evidence

ORD record
ord-e1b51719506c47b098cc0adc15b6e0ec
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

Loading…