2-Ethenyl-1-methyl-1H-pyrrole → HCID 57092295, compound

HRID 259734Notes

Reaction equation

HRID 259734 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH:7]=[CH2:8].[CH:9]([C:12]([CH3:22])([N:15]1[C:19](=[O:20])[CH:18]=[CH:17][C:16]1=[O:21])[C:13]#[N:14])([CH3:11])[CH3:10]>C(Cl)(Cl)Cl>[CH:9]([C:12]([CH3:22])([N:15]1[C:19](=[O:20])[CH:18]2[CH2:8][CH2:7][C:3]3[N:2]([CH3:1])[CH:6]=[CH:5][C:4]=3[CH:17]2[C:16]1=[O:21])[C:13]#[N:14])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 123447232-Ethenyl-1-methyl-1H-pyrroleHCID 13730721HCID 13730721, compound

Product 1

HCID 57092295HCID 57092295, compoundYield 589.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-methyl-2-vinylpyrrole (3.90 g, 36.0 mmol), α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (7.00 g, 36.0 mmol) and chloroform is stirred overnight at room temperature and concentrated in vacuo. The resultant residue is flash chromatographed (silica gel, 50% ether:hexanes eluent) to afford the title product as a clear yellow glass (63.5 g, 58.8%).

Workup

  1. concentrationconcentrated in vacuo
  2. customchromatographed (silica gel, 50% ether:hexanes eluent)

Sources & evidence

ORD record
ord-152586f9a4c645bb81fb9a2f4cb9a597
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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