Selenium Dioxide → HCID 20401026, compound

HRID 894050Notes

Reaction equation

HRID 894050 reaction equation
Cl.N1C=CC=CC=1C[N:9]1[C:13]([C:14](=[O:22])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:12][C:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:10]1.O1CCOCC1.[Se](=O)=O>O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]([C:13]2[NH:9][CH:10]=[C:11]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:12]=2)=[O:22])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 24007Selenium DioxideHCID 312751,4-DioxaneHCID 12897114HCID 12897114, compound

Product 1

HCID 20401026HCID 20401026, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl 1-(2-pyridylmethyl)-5-(4-chlorobenzoyl)-pyrrole-3-carboxylate hydrochloride (4.05 g.) was combined with 150 ml. of dioxane, 5 ml. of water and 10 g. of selenium dioxide and refluxed for 18 hours. The reaction mixture was filtered, the filtrate diluted with 150 ml. of ether and 150 ml. of water, and equilibrated. The organic phase was separated, back-washed with two 100 ml. portions of water, and concentrated to yield solid ethyl 5-(4-chlorobenzoyl)pyrrole-3-carboxylate (2.7 g., Rf 0.55 on silica gel thin layer chromatography with ethyl acetate-1/hexane-5/5% acetic acid as eluant).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate diluted with 150 ml
  3. customThe organic phase was separated
  4. washback-washed with two 100 ml
  5. concentrationportions of water, and concentrated

Sources & evidence

ORD record
ord-34c469da00b54f959a1fadc91cffc3e0
Source dataset
uspto-grants-1981_08
Patent number
US04282242

Reaction notes

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