HCID 12519688, compound → HCID 86747722, compound

HRID 439730Notes

Reaction equation

HRID 439730 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-427111d5408a4f37910295f491070023
Source dataset
uspto-grants-1996_05
Patent number
US05516751

Reaction notes

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