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

HRID 2388723
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HRID 2388723 반응식
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]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

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온도
25 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-f28757da79014f3db38549961e3af480
출처 데이터셋
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08268814B2

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