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

HRID 1366939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366939
[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]

Komponenten

6

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ea20aac31eda4aa3b860c3c6914dc89f
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893098B2

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