Selenium Dioxide → Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate

HRID 1703289Notes

Reaction equation

HRID 1703289 reaction equation
N1C=CC=CC=1C[N:8]1[C:12]([C:13](=[O:26])[C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)=[CH:11][C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[CH:9]1.O1CCOCC1.[Se](=O)=O>O>[C:20]1([C:17]2[CH:16]=[CH:15][C:14]([C:13]([C:12]3[NH:8][CH:9]=[C:10]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:11]=3)=[O:26])=[CH:19][CH:18]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 20401013Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate

Product 1

HCID 12897070Ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylateYield 75.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 1-(2-pyridylmethyl)-5-(4-phenylbenzoyl)pyrrole-3-carboxylate (5.3 g.) was combined with 150 ml. of dioxane, 5 ml. of water and 10 g. of selenium dioxide and refluxed for approximately 16 hours. Insoluble material was separated by filtration, the filtrate was diluted with 150 ml. of ether and 150 ml. of water, the mixture equilibrated, the ether phase separated, back-washed twice with 100 ml. portions of water, filtered and concentrated to yield ethyl 5-(4-phenylbenzoyl)pyrrole-3-carboxylate (3.1 g, solid; Rf 0.4 on silica gel thin layer chromatography with ethyl acetate-1/hexane-5/5% acetic acid as eluant).

Workup

  1. customInsoluble material was separated by filtration
  2. additionthe filtrate was diluted with 150 ml
  3. customthe ether phase separated
  4. washback-washed twice with 100 ml
  5. filtrationportions of water, filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-f7862f327ca449be806e976b49e06bff
Source dataset
uspto-grants-1982_09
Patent number
US04351843

Reaction notes

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