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

HRID 642235노트

반응식

HRID 642235 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 684260441-(4-Fluoro-phenyl)-2-methyl-4-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester수율 52.4%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-1982848e66a8474b86a06d4f16ccc0a9
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696223B2

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