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

HRID 1385571
ノート
印刷プレビュー

反応式

HRID 1385571 の反応式
[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]
参加物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 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 5486782-Azabicyclo(2.2.1)hept-5-en-3-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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%.

後処理

  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

出典と根拠

ORDレコード
ord-9f5e255960c241d99599b24702e5b3dd
出典データセット
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06262295B1

反応ノート

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