Water → 5-(4-Fluoro-phenyl)-2-methyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester

HRID 642218Notes

Reaction equation

HRID 642218 reaction equation
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:9][C:10]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=O)[C:6](=O)[CH3:7])[CH3:2].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[N:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:6]=1[CH3:7])=[O:19])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 141739732-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl ester

Product 1

HCID 143391945-(4-Fluoro-phenyl)-2-methyl-1-phenyl-1H-pyrrole-3-carboxylic acid ethyl esterYield 79.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 2-[2-(4-fluoro-phenyl)-2-oxo-ethyl]-3-oxo-butyric acid ethyl ester (6.979 g, 26.21 mmol)), aniline (2.9 mL, 31.45 mmol) and p-toluenesulfonic acid (TsOH) monohydrate (249 mg, 1.31 mmol) in toluene (60 mL) was refluxed overnight while the generated water was separated with Dean-Stark distillation head. Then the reaction mixture was diluted with EtOAc, washed with saturated sodium hydrogen carbonate aqueous solution, and saturated sodium chloride aqueous solution, respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, the residue was purified with column chromatography to give the title compound (6.768 g); The title compound, ESI MS (m/z): 324 (M+H+).

Workup

  1. customwas separated with Dean-Stark distillation head
  2. additionThen the reaction mixture was diluted with EtOAc
  3. washwashed with saturated sodium hydrogen carbonate aqueous solution, and saturated sodium chloride aqueous solution
  4. dry with materialrespectively, the organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified with column chromatography

Sources & evidence

ORD record
ord-dcb928c138ce4bef956c9abfad82b96c
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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