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Water → 2-Acetyl-2-azabicyclo[2.2.1]hept-5-en-3-one

HRID 1274418
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HRID 1274418 반응식
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[C:3](=[O:8])[NH:2]2.N1C=CC=CC=1.[C:15](Cl)(=[O:17])[CH3:16].O>C(#N)C>[C:15]([N:2]1[C:3](=[O:8])[CH:4]2[CH2:7][CH:1]1[CH:6]=[CH:5]2)(=[O:17])[CH3:16]
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참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

생성물 1

HCID 113555782-Acetyl-2-azabicyclo[2.2.1]hept-5-en-3-one수율 77.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

100 g of (±)-2-azabicyclo[2.2.1]hept-5-en-3-one were dissolved in acetonitrile (800 ml) and pyridine (161.26 ml) under nitrogen. At 12° C., 104.5 g of acetyl chloride were added dropwise over the course of 2 hours. The mixture was then stirred at room temperature for 4.5 hours. 800 ml of water were added to the mixture, and the acetonitrile was evaporated off in vacuo. The aqueous phase was extracted 3 times with 400 ml of ethyl acetate. The combined org. phases were washed with 1N HCl (400 ml), water (400 ml), saturated NaCl (400 ml), dried with magnesium sulphate and completely evaporated. The residue was taken up in methylene chloride and filtered through silica gel. The filtrate was concentrated and the product was purified by distillation. 107.76 g of product were obtained as a clear liquid. The yield was 71%.

후처리

  1. customthe acetonitrile was evaporated off in vacuo
  2. extractionThe aqueous phase was extracted 3 times with 400 ml of ethyl acetate
  3. washphases were washed with 1N HCl (400 ml), water (400 ml), saturated NaCl (400 ml)
  4. dry with materialdried with magnesium sulphate
  5. customcompletely evaporated
  6. filtrationfiltered through silica gel
  7. concentrationThe filtrate was concentrated
  8. distillationthe product was purified by distillation

출처 및 근거

ORD 기록
ord-b75b8a95ae6042bba0cf48bb8b0830d0
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06156893

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