1,3-Cyclohexadiene → Bicyclo[2.2.2]oct-5-en-2-one

HRID 220238

반응식

HRID 220238 반응식
C([O:4][C:5](=[CH2:8])[C:6]#N)(=O)C.[CH:9]1[CH2:14][CH2:13]C=[CH:11][CH:10]=1>C(Cl)Cl>[CH:6]12[CH2:13][CH2:14][CH:9]([CH:10]=[CH:11]1)[CH2:4][C:5]2=[O:8]

참가 물질

4

반응물 2

HCID 116051,3-CyclohexadieneHCID 182911-Cyanovinyl acetate

생성물 1

HCID 137507Bicyclo[2.2.2]oct-5-en-2-one수율 20.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

A mixture of 7.0 g of α-acetoxyacrylonitrile and 3.2 g of 1,3-cyclohexadiene was heated in a closed microwave tube at 90° C. for 24 h. The obtained brown oil was taken up in DCM and evaporated. The crude mixture was washed over a pad of Celite (2 cm) using 300 mL of Hept-EtOAc (9:1) and then concentrated in vacuo. The yellow oil was redissolved in 10 mL DMSO and 3.2 g of KOH, dissolved in 5 mL water, was carefully added. The resulting black mixture was stirred for 2 d at rt, diluted with water and extracted 3 times with Hept. The combined organic phases were washed 3 times with brine, dried over Na2SO4 and concentrated in vacuo to obtain 1.0 g of rac-(1R*,4R*)-bicyclo[2.2.2]oct-5-en-2-one as beige solid.

후처리

  1. customevaporated
  2. washThe crude mixture was washed over a pad of Celite (2 cm)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe yellow oil was redissolved in 10 mL DMSO
  5. dissolution3.2 g of KOH, dissolved in 5 mL water
  6. additionwas carefully added
  7. additiondiluted with water
  8. extractionextracted 3 times with Hept
  9. washThe combined organic phases were washed 3 times with brine
  10. dry with materialdried over Na2SO4
  11. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-790ee73cd05b4e1e8a7c970a6916e2c1
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202885B2

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