Water → 1-(4-Fluoro-phenyl)-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 642235Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642235
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:17](=O)[CH3:18])[CH:6]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:7][N+:8]([O-])=O)[CH3:2].[F:21][C:22]1[CH:28]=[CH:27][C:25](N)=[CH:24][CH:23]=1.O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[C:6]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:7][N:8]([C:25]2[CH:27]=[CH:28][C:22]([F:21])=[CH:23][CH:24]=2)[C:17]=1[CH3:18])=[O:20])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 97314-FluoroanilineHCID 11323434Ethyl 2-acetyl-4-nitro-3-phenylbutanoate

Produkt 1

HCID 684260441-(4-Fluoro-phenyl)-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl esterAusbeute 52,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 2-acetyl-4-nitro-3-phenyl-butyric acid ethyl ester (4.26 g, 14.3 mmol), 4-fluoroaniline (1.75 g, 15.73 mmol), and TsOH monohydrate (136 mg, 0.72 mmol) in toluene (40 mL) was refluxed overnight, while the generated water was collected with a Dean-Stark distillation head; then the reaction was cooled, diluted with EtOAc, washed with diluted sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution respective, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, the residue was purified on column to give the desired title compound (2.422 g); ESI MS (m/z): 324 (M+H+).

Aufarbeitung

  1. distillationwas collected with a Dean-Stark distillation head
  2. temperaturethen the reaction was cooled
  3. additiondiluted with EtOAc
  4. washwashed with diluted sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution respective
  5. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified on column

Quellen und Nachweise

ORD-Eintrag
ord-1982848e66a8474b86a06d4f16ccc0a9
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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