Water → 1-(4-Fluoro-phenyl)-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester
Reaction equation
[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]Participants
5
Procedure
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+).
Workup
- distillationwas collected with a Dean-Stark distillation head
- temperaturethen the reaction was cooled
- additiondiluted with EtOAc
- washwashed with diluted sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution respective
- dry with materialthe organic phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customthe residue was purified on column
Sources & evidence
- ORD record
- ord-1982848e66a8474b86a06d4f16ccc0a9
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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