Sodium hydride → N-ethoxyethyl-2-trifluoroacetylpyrrole

HRID 1452544ノート

反応式

HRID 1452544 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 68869870N-ethoxyethyl-2-trifluoroacetylpyrrole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-62399ae0e6354cc889c73797f0fb03c1
出典データセット
uspto-grants-2009_01
特許番号
US07473703B2

反応ノート

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