2-(Trichloroacetyl)pyrrole → 1-[5-(Trichloroacetyl)-1H-pyrrol-3-yl]propan-1-one

HRID 351609Notes

Reaction equation

HRID 351609 reaction equation
[Cl:1][C:2]([Cl:11])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Cl:11][C:2]([Cl:1])([Cl:10])[C:3]([C:5]1[NH:6][CH:7]=[C:8]([C:3](=[O:4])[CH2:5][CH3:9])[CH:9]=1)=[O:4]

Participants

4

Reactant 2

HCID 3214872-(Trichloroacetyl)pyrroleHCID 6451240Aluminum(III) Chloride

Product 1

HCID 27685511-[5-(Trichloroacetyl)-1H-pyrrol-3-yl]propan-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a dry flask, 3-proprionyl chloride (1 equivalent) was combined with 2-trichloroacetyl pyrrole (1 equivalent) in a minimum amount of dichloromethane (DCM). To the resulting solution, at ambient temperature, was added aluminum trichloride (1 equivalent). After 2 hours, the reaction mixture was applied directly onto a silica gel column. Gradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 3.

Workup

  1. washGradient elution with 10% ethyl acetate to 50% ethyl acetate in hexanes provided compound 3

Sources & evidence

ORD record
ord-cdd1c2ef92f641ecbeaca80ea630cf62
Source dataset
uspto-grants-2004_06
Patent number
US06743791B2

Reaction notes

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