4-Pyridinecarboxaldehyde → 2-[2-(4-Pyridyl)ethenyl]-1-nitrobenzene

HRID 1741012

反応式

HRID 1741012 の反応式
[Br-].[N+:2]([C:5]1[CH:30]=[CH:29][CH:28]=[CH:27][C:6]=1[CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O-:4])=[O:3].C([Li])CCC.CCCCCC.[CH:42](=O)[C:43]1[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=1>C1C=CC=CC=1>[N:46]1[CH:47]=[CH:48][C:43]([CH:42]=[CH:7][C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N+:2]([O-:4])=[O:3])=[CH:44][CH:45]=1

参加物

5

反応物 3

HCID 133894-PyridinecarboxaldehydeHCID 10885283(2-Nitrobenzyl)triphenylphosphonium bromideHCID 178418244HCID 178418244、化合物

生成物 1

HCID 543300572-[2-(4-Pyridyl)ethenyl]-1-nitrobenzene収率 44.6%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

In 120 ml of benzene was suspended 12.00 g of 2-nitrobenzyltriphenylphosphonium bromide and, under argon gas, 20 ml of 1.6M n-butyllithium/n-hexane was added dropwise under ice-cooling with care exercised so that the internal temperature would not rise beyond 20° C. The mixture was then stirred at room temperature for 2 hours, after which 3.05 g of isonicotinaldehyde was added dropwise under ice-cooling and the mixture was stirred at room temperature for another 4 hours. This reaction mixture was poured upon ice-water and extracted with ether. This extract was evaporated under reduced pressure to remove the solvent and the residue was diluted with chloroform and extracted with 2N-hydrochloric acid. The aqueous layer was made basic by adding 30% aqueous sodium hydroxide solution and extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and the solvent was evaporated off. The residue was purified by silica gel column chromatography (chloroform alone) to provide 2.53 g of the title compound as tan-colored oil. This product was subjected to the next reaction without further purification.

後処理

  1. temperaturecooling with care
  2. customrise beyond 20° C
  3. temperaturecooling
  4. stirringthe mixture was stirred at room temperature for another 4 hours
  5. extractionextracted with ether
  6. customThis extract was evaporated under reduced pressure
  7. customto remove the solvent
  8. additionthe residue was diluted with chloroform
  9. extractionextracted with 2N-hydrochloric acid
  10. additionby adding 30% aqueous sodium hydroxide solution
  11. extractionextracted with chloroform
  12. extractionThe chloroform extract
  13. dry with materialwas dried over anhydrous magnesium sulfate
  14. customthe solvent was evaporated off
  15. customThe residue was purified by silica gel column chromatography (chloroform alone)

出典と根拠

ORDレコード
ord-168a0824b7be4e83adfc4f5e133f4b17
出典データセット
uspto-grants-1999_10
特許番号
US05972976

関連ノート

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