2-(Trichloroacetyl)pyrrole → HCID 22713586, compound

HRID 968548Notes

Reaction equation

HRID 968548 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 7. 1H NMR consistent with structure.

Workup

  1. customthe crude mixture was chromatographed on silica gel (MeOH 2% in DCM)

Sources & evidence

ORD record
ord-c5785535545c41afb90d9ddbbfe07903
Source dataset
uspto-grants-2007_12
Patent number
US07304061B2

Reaction notes

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