Dimethylformamide → 5-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one

HRID 440570

反応式

HRID 440570 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]2[CH2:13][CH2:12][CH:11]([CH3:14])[C:10]2=[O:15])=[CH:6][CH:5]=1.[H][H].[CH3:20]N(C)C=O>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH:8]=[C:9]2[CH2:13][CH2:12][C:11]([CH3:20])([CH3:14])[C:10]2=[O:15])=[CH:16][CH:17]=1

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 537529512-Methyl-5-(4-chlorobenzylidene)-cyclopentanoneHCID 178418361HCID 178418361、化合物

生成物 1

HCID 534210215-[(4-Chlorophenyl)methylidene]-2,2-dimethylcyclopentan-1-one

実験手順

2.4 g of sodium hydride (60% oily sodium hydride washed with anhydrous benzene) was added to 100 ml of anhydrous dimethylformamide under nitrogen atmosphere while stirring. 24 g of 2-(4-chlorobenzylidene)-5-methylcylopentanone (prepared in Example 3) was added to the mixture, followed by stirring at room temperature until generation of hydrogen was terminated. After the addition of 15 g of methyl iodide, the mixture was stirred for a further 2 hours at 60° C. The reaction mixture thus obtained was allowed to cool, poured into ice water, and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure. The residue was solidified with the addition of a small amount of hexane to obtain the title compound.

後処理

  1. customwas terminated
  2. additionAfter the addition of 15 g of methyl iodide
  3. stirringthe mixture was stirred for a further 2 hours at 60° C
  4. customThe reaction mixture thus obtained
  5. temperatureto cool
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customfollowed by evaporation of the solvent under reduced pressure
  10. additionThe residue was solidified with the addition of a small amount of hexane

出典と根拠

ORDレコード
ord-13e78230d0394daea8293c09e32694d9
出典データセット
uspto-grants-1996_05
特許番号
US05519160

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