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Dimethylformamide → Ethyl 4-chloro-3-formyl-5,6-dihydro-2H-pyridine-1-carboxylate

HRID 2388723
ノート
印刷プレビュー

反応式

HRID 2388723 の反応式
O=P(Cl)(Cl)[Cl:3].CN([CH:9]=[O:10])C.[CH2:11]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][C:17]1=O)=[O:15])[CH3:12].C([O-])(=O)C.[Na+]>O>[Cl:3][C:19]1[CH2:20][CH2:21][N:16]([C:14]([O:13][CH2:11][CH3:12])=[O:15])[CH2:17][C:18]=1[CH:9]=[O:10]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 13303317Ethyl 2-oxopiperidine-1-carboxylate

生成物 1

HCID 3024580Ethyl 4-chloro-3-formyl-5,6-dihydro-2H-pyridine-1-carboxylate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

POCl3 (2.18 g, 23.4 mmol) was added very slowly to 2.7 ml of dry DMF at 0° C. The mixture obtained was stirred at 25° C. for 15 minutes. After the reaction temperature had been reduced again to 0° C., N-ethoxycarbonylpiperidone (11.7 mmol) was added. The reaction mixture obtained was stirred at 25° C. for 3 hours. Thereafter, sodium acetate (7 g) and water (8.5 ml) were added and the mixture was stirred. The reaction mixture was extracted with benzene. The organic phase was washed successively with water, sodium carbonate and saturated sodium chloride solution. After the organic phase had been dried over sodium sulfate, the solvent was removed under reduced pressure. The crude product obtained was employed in the next stage without further purification. The crude yield was 63%.

後処理

  1. customThe mixture obtained
  2. customhad been reduced again to 0° C.
  3. customThe reaction mixture obtained
  4. stirringwas stirred at 25° C. for 3 hours
  5. stirringthe mixture was stirred
  6. extractionThe reaction mixture was extracted with benzene
  7. washThe organic phase was washed successively with water, sodium carbonate and saturated sodium chloride solution
  8. dry with materialAfter the organic phase had been dried over sodium sulfate
  9. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-f28757da79014f3db38549961e3af480
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08268814B2

反応ノート

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