Pyrrole → 5-Chloro-1-(1H-pyrrol-2-yl)-1-pentanone

HRID 1276284Notes

Reaction equation

HRID 1276284 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](Cl)=[O:11].[NH:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1>ClCCCl>[Cl:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([C:14]1[NH:13][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 8027PyrroleHCID 740895-Chlorovaleryl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 101038875-Chloro-1-(1H-pyrrol-2-yl)-1-pentanone

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 26.7 g (0.200 mol) of aluminium chloride and 31 g (0.200 mol) of 5-chlorovaleryl chloride in 200 ml of 1,2-dichloroethane is added slowly to a solution of 13.4 g (0.200 mol) of pyrrole in 250 ml of 1,2-dichloroethane. The reaction medium is stirred for 2 h at room temperature and is poured onto ice-cold hydrochloric acid. After extraction with methylene chloride, a red-brown oil is obtained.

Workup

  1. additionis poured onto ice-cold hydrochloric acid
  2. extractionAfter extraction with methylene chloride
  3. customa red-brown oil is obtained

Sources & evidence

ORD record
ord-7ae910d74cad4b3badd23967fdaf577c
Source dataset
uspto-grants-2000_12
Patent number
US06166035

Reaction notes

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