4-Chlorophenylacetyl chloride → 4-[2-(4-Chloro-phenyl)-acetyl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

HRID 1434790Notes

Reaction equation

HRID 1434790 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]([C:17]1[NH:18][CH:19]=[CH:20][C:21]=1[CH3:22])=[O:16])[CH3:13].[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.ClCCCl>[CH2:12]([O:14][C:15]([C:17]1[NH:18][CH:19]=[C:20]([C:9](=[O:10])[CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:21]=1[CH3:22])=[O:16])[CH3:13]

Participants

6

Reactant 3

HCID 906924-Chlorophenylacetyl chlorideHCID 5324582Ethyl 3-methyl-1H-pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 574351104-[2-(4-Chloro-phenyl)-acetyl]-3-methyl-1H-pyrrole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (4-chlorophenyl)-acetyl chloride (3 mmol) in dichloromethane or 1,2-dichloroethane (4 ml) was added to a solution cooled at −40° C. of 84 (0.229 g, 1.5 mmol) and AlCl3 was added (0.400 g, 3 mmol). The reaction mixture was stirred for 30 minutes at the same temperature. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with NaOH (2 M) and brine, dried over Na2SO4, and evaporated to dryness under vacuum to give crude product 85. Crude yield: 96%

Workup

  1. additionwas added (0.400 g, 3 mmol)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with NaOH (2 M) and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-752b154c019741038a28c108b778c8e9
Source dataset
uspto-grants-2009_11
Patent number
US07615572B2

Reaction notes

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