HCID 12519688, compound → HCID 86747722, compound

HRID 259732Notes

Reaction equation

HRID 259732 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([CH:7]=[CH2:8])=[CH:3]1.[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][CH:4]3[CH2:5][CH2:6][N:2]([CH3:1])[C:3]3=[C:17]2[C:16]1=[O:21])[C:13]#[N:14])([CH3:11])[CH3:10]

Participants

4

Reactant 2

HCID 12519688HCID 12519688, compoundHCID 13730721HCID 13730721, compound

Product 1

HCID 86747722HCID 86747722, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 1-methyl-3-vinylpyrrole (9.50 g, 0.089 mol), α-isopropyl-α-methyl-2,5-dioxo-3-pyrroline-1-acetonitrile (17.0 g, 0.089 mol) and chloroform is stirred overnight at room temperature and concentrated in vacuo to an amber oil residue. The residue is flash chromatographed (silica gel, gradient elution: 50% hexanes: methylene chloride to ether) to afford the title product as an orange glass (13.0 g, 48.8%), identified by 1HNMR spectroscopy.

Workup

  1. concentrationconcentrated in vacuo to an amber oil residue
  2. customchromatographed
  3. wash(silica gel, gradient elution: 50% hexanes: methylene chloride to ether)

Sources & evidence

ORD record
ord-c746ce8d3dc344b7a42af56c9ac22dcd
Source dataset
uspto-grants-1996_06
Patent number
US05523279

Reaction notes

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