Methyl vinyl ketone → {[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl]oxy}acetonitrile

HRID 569304노트

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HRID 569304 반응식
[C:1]([O:4][CH2:5][CH2:6][CH:7]1[CH2:15][C:14]2[C:9](=[C:10]([Cl:21])[C:11]([Cl:20])=[C:12]([O:16][CH2:17][C:18]#[N:19])[CH:13]=2)[C:8]1=[O:22])(=[O:3])[CH3:2].N12CCCC1=CCCN2.[CH:32]([C:34]([CH3:36])=[O:35])=[CH2:33].C(OCC)(=O)C>O1CCCC1.N12CCCC1=CCCN2.C(O)(=O)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1([CH2:33][CH2:32][C:34](=[O:35])[CH3:36])[CH2:15][C:14]2[C:9](=[C:10]([Cl:21])[C:11]([Cl:20])=[C:12]([O:16][CH2:17][C:18]#[N:19])[CH:13]=2)[C:8]1=[O:22])(=[O:3])[CH3:2]

참가 물질

8

반응물 4

HCID 6570Methyl vinyl ketone2회HCID 8857Ethyl AcetateHCID 20148936{[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetonitrileHCID 21585024Diazabicyclo[4.3.0]non-5-ene

생성물 1

HCID 20148940{[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-2-(3-oxobutyl)-1H-inden-5-yl]oxy}acetonitrile

시약·촉매·용매 3

HCID 21585024Diazabicyclo[4.3.0]non-5-ene촉매HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

{[2-(2-Acetoxyethyl)-6,7-dichloro-2,3-dihydro-1-oxo-1H-inden-5-yl]oxy}acetonitrile (3.42 g, 10 mMole) is dissolved in tetrahydrofuran (30 ml), warmed to 40° C. and diazabicyclo[4.3.0]non-5-ene (50 microliters) added. Then methyl vinyl ketone (1.2 g, 17 mMole) is added and the mixture stirred at 50°-52° C. for two hours. More methyl vinyl ketone (600 mg) and diazabicyclo[4.3.0]non-5-ene (2 drops) are added and stirring and heating continued for another 2 hours. The solution is cooled, treated with ethyl acetate (50 ml) and poured into ice water (250 ml) containing acetic acid (1 ml). The organic layer is separated and the aqueous layer extracted first with methylene chloride and then with ether. The combined organic layers were dried over MgSO4 and the solvent removed by evaporation in vacuo to give the desired product.

후처리

  1. stirringstirring
  2. temperatureheating
  3. waitcontinued for another 2 hours
  4. temperatureThe solution is cooled
  5. customThe organic layer is separated
  6. extractionthe aqueous layer extracted first with methylene chloride
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customthe solvent removed by evaporation in vacuo

출처 및 근거

ORD 기록
ord-a44c4640c76245ea9b3702fd97263d87
출처 데이터셋
uspto-grants-1988_03
특허 번호
US04731471

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