Ethanol → Ethyl 4-phenyl-1H-pyrrole-2-carboxylate

HRID 880438Notes

Reaction equation

HRID 880438 reaction equation
[Na].Cl.[CH3:3][O:4][C:5](=[O:8])[CH2:6][NH2:7].Cl([O-])(=O)(=O)=O.CN(C)[CH:16]=[C:17]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:18]=[N+](C)C.[CH2:29](O)C>>[C:22]1([C:17]2[CH:16]=[C:6]([C:5]([O:4][CH2:3][CH3:29])=[O:8])[NH:7][CH:18]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 122755Glycine methyl ester hydrochlorideHCID 5360545SodiumHCID 78294239(3-Dimethylamino-2-phenyl-prop-2-enylidene)-dimethyl-ammonium perchlorate

Product 1

HCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylateYield 57%

Procedure

Sodium metal (900 mg, 41.0 mmol) was added to dry ethanol (150 mL) and allowed to dissolve over 30 min. Glycine methyl ester hydrochloride (3.2 g, 25.0 mmol) and (3-dimethylamino-2-phenyl-prop-2-enylidene)-dimethyl-ammonium perchlorate (5.0 g, 16.0 mmol) were added successively and the reaction mixture heated at reflux for 16 h. Ethanol was evaporated in vacuo, the residue diluted with water and extracted with chloroform. The organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The crude product obtained was purified by column chromatography over neutral alumina using 10% ethyl acetate in petroleum ether as eluent to afford ethyl 4-phenyl-1H-pyrrole-2-carboxylate (2.0 g, 57%) as a solid.

Workup

  1. dissolutionto dissolve over 30 min
  2. temperaturethe reaction mixture heated
  3. temperatureat reflux for 16 h
  4. customEthanol was evaporated in vacuo
  5. additionthe residue diluted with water
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with water, brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product obtained
  12. customwas purified by column chromatography over neutral alumina using 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-6fd970e7f2bd41ccac97e96abe1565e9
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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