2,4-Dimethylpyrrole → (3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone

HRID 2120227Notes

Reaction equation

HRID 2120227 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:10](Cl)=[O:11].[CH3:18][C:19]1[NH:20][CH:21]=[C:22]([CH3:24])[CH:23]=1>ClCCl.C(OCC)(=O)C>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([C:10]([C:21]2[NH:20][C:19]([CH3:18])=[CH:23][C:22]=2[CH3:24])=[O:11])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17]

Participants

6

Reactant 3

HCID 395392,4-DimethylpyrroleHCID 77070Veratroyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 23439089(3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanoneYield 39%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Aluminum chloride (1.7 g, 12.75 mmol) in dichloromethane (100 mL) was added to the 3,4-dimethoxybenzoyl chloride (2.0 g, 10 mmol) at room temperature, followed by a solution of 2,4-dimethylpyrrole (1.5 g, 15.8 mmol) in dichloromethane (5 mL). The mixture was then stirred at room temperature for overnight. The reaction was diluted with ethyl acetate, washed with brine, dried and concentrated. The residue was chromatographed eluting with ethyl acetate and hexane to give 1 g (39%) of (3,4-dimethoxy-phenyl)-(3,5-dimethyl-1H-pyrrol-2-yl)-methanone as a solid.

Workup

  1. washwashed with brine
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was chromatographed
  5. washeluting with ethyl acetate and hexane

Sources & evidence

ORD record
ord-49fd1e16b30d48dab7626e371784391e
Source dataset
uspto-grants-2004_02
Patent number
US06689806B1

Reaction notes

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