Water → 4-(2,5-Dihydro-1H-pyrrole-1-carbonyl)-3-methylbenzonitrile

HRID 2053753ノート

反応式

HRID 2053753 の反応式
[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=2[CH3:15])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1.[Cu](C#N)[C:17]#[N:18].O.C(OCC)(=O)C>CN(C)C=O>[N:1]1([C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:17]#[N:18])=[CH:10][C:9]=2[CH3:15])=[O:7])[CH2:5][CH:4]=[CH:3][CH2:2]1

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 22600480(4-Bromo-2-methylphenyl)(2,5-dihydro-1H-pyrrol-1-yl)methanoneHCID 178418260HCID 178418260、化合物

生成物 1

HCID 226004824-(2,5-Dihydro-1H-pyrrole-1-carbonyl)-3-methylbenzonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
140 °C

実験手順

31.6 g (0.11 mol) of 4-(2,5-dihydropyrrol-1-ylcarbonyl)-3-methylbromobenzene is dissolved in 125 mL of dimethylformamide and combined with 20.2 g (0.23 mol) of copper cyanide and 3.2 g (2.7 mmol) of tetrakis-triphenylphosphinepalladium(0). The suspension is stirred for 20 hours at 140° C. Then it is cooled to 80° C., combined with 150 mL of water, 150 mL of ethyl acetate, and 25 g of CELITE® filter aid and filtered through CELITE® filter aid. The organic phase is separated off, washed with sodium chloride solution, dried over sodium sulfate, and concentrated by evaporation. The residue is chromatographed on silica gel, eluting with ethyl acetate/ethanol (50:1 and 19:1). The corresponding fractions are combined and concentrated by evaporation. Yield: 11.7 g (49% of theory); Rf value: 0.55 (silica gel; ethyl acetate/ethanol=9:1).

後処理

  1. temperatureThen it is cooled to 80° C.
  2. filtrationfilter aid
  3. filtrationfiltered through CELITE®
  4. filtrationfilter aid
  5. customThe organic phase is separated off
  6. washwashed with sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation
  9. customThe residue is chromatographed on silica gel
  10. washeluting with ethyl acetate/ethanol (50:1 and 19:1)
  11. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-fc94ac9fc4c046f4bf3b57cbbd5699c5
出典データセット
uspto-grants-2008_02
特許番号
US07326791B2

反応ノート

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