Dimethylformamide → 1-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde

HRID 556730

反応式

HRID 556730 の反応式
O=P(Cl)(Cl)Cl.CN([CH:9]=[O:10])C.[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)([O-:13])=[O:12].CC([O-])=O.[Na+]>C(Cl)(Cl)(Cl)Cl.O>[N+:11]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH:9]=[O:10])([O-:13])=[O:12]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 5206111-(2-Nitrophenyl)pyrrole

生成物 1

HCID 47153911-(2-nitrophenyl)-1H-pyrrole-2-carbaldehyde収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 5943Carbon Tetrachloride溶媒2 回

実験手順

POCl3 was added to DMF at 0-10° C. after which 50 ml of CCl4 was added at room temperature. A solution of 4.5 g (24 mmol) 1a in 50 ml of CCl4 was added slowly to the reaction mixture at about 10° C. during 1 hour. The reaction mixture was refluxed for 15 min. and a solution of 50 g of NaOAc, 3H2O in 50 ml of H2O was added and refluxing was continued for 15 min. The mixture was cooled, extracted with ether and dried over Na2SO4. 8.0 g (65%) of 2a was isolated by column chromatography using EtOAc:petroleum ether as eluent.

後処理

  1. additionwas added at room temperature
  2. temperatureThe reaction mixture was refluxed for 15 min.
  3. temperaturerefluxing
  4. temperatureThe mixture was cooled
  5. extractionextracted with ether
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-e51942fef4734edd9a97c030c059bd16
出典データセット
uspto-grants-2011_11
特許番号
US08058306B2

関連ノート

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