Selenium Dioxide → HCID 20401026, compound

HRID 1981002Notes

Reaction equation

HRID 1981002 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-c2c7faf39f3f49a183441d04c5dfd1c8
Source dataset
uspto-grants-1985_04
Patent number
US04511576

Reaction notes

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