Sodium hydride → N-ethoxyethyl-2-trifluoroacetylpyrrole

HRID 2053678노트

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HRID 2053678 반응식
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]([C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)=[O:6].[CH2:14]([O:16][CH2:17][CH2:18]Br)[CH3:15]>CN(C=O)C>[CH2:14]([O:16][CH2:17][CH2:18][N:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5](=[O:6])[C:4]([F:3])([F:12])[F:13])[CH3:15]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 611412-Bromoethyl ethyl etherHCID 137637Ethanone, 2,2,2-trifluoro-1-(1H-pyrrol-2-yl)-

생성물 1

HCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrrole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a suspension of 268 mg (6.70 mmol) of NaH (60% dispersion in oil) in 20 mL DMF at 0° C. was added 1.01 g (6.19 mmol) of 2-(trifluoroacteyl)pyrrole and the mixture was stirred at 0° C. for 1 h. After this time, 765 μL (6.51 mmol) of 2-bromoethyl ethyl ether was added and the mixture was warmed to 60° C. and stirred for 16 h. After this time, the reaction mixture was allowed to cool to room temperature, quenched by the addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography on silica gel (pure hexanes grading to hexanes:EtOAc, 97:3) to give the title compound.

후처리

  1. temperaturethe mixture was warmed to 60° C.
  2. stirringstirred for 16 h
  3. temperatureto cool to room temperature
  4. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  5. extractionextracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated
  10. customThe residue was purified by chromatography on silica gel (pure hexanes grading to hexanes:EtOAc, 97:3)

출처 및 근거

ORD 기록
ord-37815230ee7a4d879efdd736056f2ec9
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07326812B2

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