2-(Trichloroacetyl)pyrrole → HCID 22713586, compound

HRID 852303Notes

Reaction equation

HRID 852303 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].[CH3:12][O:13][CH2:14][CH2:15][C:16](Cl)=[O:17].[Cl-].[Cl-].[Cl-].[Al+3]>C(Cl)Cl>[CH3:12][O:13][CH2:14][CH2:15][C:16]([C:8]1[CH:9]=[C:5]([C:3](=[O:4])[C:2]([Cl:1])([Cl:10])[Cl:11])[NH:6][CH:7]=1)=[O:17]

Participants

5

Reactant 3

HCID 3214872-(Trichloroacetyl)pyrroleHCID 27597283-Methoxypropanoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 22713586HCID 22713586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-trichloroacetyl pyrrole (1.0 equivalent, 4.67 g, 22 mmol) in methylene chloride (5 mL) was added 3-methoxypropionyl chloride (1.0 equivalent, 22 mmol) then aluminium trichloride (1.0 equivalent, 2.93 g, 22 mmol) was added in small portions. After 2.5 hours, the crude mixture was chromatographed on silica gel (MeOH 2% in DCM) to afford 3.0 g of the Friedel-Craft product. 1H NMR consistent with structure.

Workup

  1. customthe crude mixture was chromatographed on silica gel (MeOH 2% in DCM)
  2. customto afford 3.0 g of the Friedel-Craft product

Sources & evidence

ORD record
ord-0bd12d2689914eb0a50ebc280adb0eaf
Source dataset
uspto-grants-2007_08
Patent number
US07253187B2

Reaction notes

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