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

HRID 569304ノート

反応式

HRID 569304 の反応式
[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]

参加物

8

反応物 4

HCID 6570Methyl vinyl ketone2 回HCID 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 21585024Diazabicyclo[4.3.0]non-5-ene触媒HCID 176Acetic Acid溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

{[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.

後処理

  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

出典と根拠

ORDレコード
ord-a44c4640c76245ea9b3702fd97263d87
出典データセット
uspto-grants-1988_03
特許番号
US04731471

反応ノート

読み込み中…