Glycine ethyl ester → Ethyl 4-phenyl-1H-pyrrole-2-carboxylate

HRID 1178116Notes

Reaction equation

HRID 1178116 reaction equation
[Na].[CH3:2][CH2:3][O:4][C:5]([CH2:7][NH2:8])=[O:6].CN(C)[CH:11]=[C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:13]=[N+](C)C.Cl([O-])(=O)(=O)=O>O.CCO>[CH2:3]([O:4][C:5]([C:7]1[NH:8][CH:11]=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:13]=1)=[O:6])[CH3:2]

Participants

7

Reactant 4

HCID 12176Glycine ethyl esterHCID 123351PerchlorateHCID 3268880(3-Dimethylamino-2-phenyl-allylidene)-dimethyl-ammoniumHCID 5360545Sodium

Product 1

HCID 14643813Ethyl 4-phenyl-1H-pyrrole-2-carboxylateYield 31.83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium metal (119 mg, 5.1 mmol) was added to EtOH (15 mL) and stirred for 30 minutes. Glycine ethyl esater hydrochloride (345 mg, 2.47 mmol) and (3-dimethylamino-2-phenyl-allylidene)-dimethyl-ammonium; perchlorate (500 mg, 1.65 mmol) was then added. The resulting mixture was stirred and heated to reflux for 2 hrs. Evaporated the reaction mixture to get the residue. The residue was diluted with cold water and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to get the residue. The residue obtained was purified by column chromatography (using silicagel of 60-120 mesh and 10% EtOAc in Hexane as eluent) to afford 113 mg (31.83% yield) of 4-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester. LCMS Purity: 98.96%. 1H NMR (CDCl3): δ 9.2 (bs, 1H), 7.58 (d, 2H), 7.42 (t, 2H), 7.26 (m, 3H), 4.4 (q, 2H), 1.4 (t, 3H).

Workup

  1. stirringThe resulting mixture was stirred
  2. temperatureheated
  3. temperatureto reflux for 2 hrs
  4. customEvaporated the reaction mixture
  5. customto get the residue
  6. extractionextracted with EtOAc
  7. washThe organic layer was washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto get the residue
  11. customThe residue obtained
  12. customwas purified by column chromatography (using silicagel of 60-120 mesh and 10% EtOAc in Hexane as eluent)

Sources & evidence

ORD record
ord-0e33696426fe466abba743dc17e179dd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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