Diethyl Malonate → 5-(5-Chloro-2-methoxyphenyl)cyclohexane-1,3-dione

HRID 1700712ノート

反応式

HRID 1700712 の反応式
[O-:1][CH2:2][CH3:3].[Na+].C(OCC)(=O)CC(OCC)=O.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:28][CH3:29])=[C:21]([CH:23]=[CH:24][C:25](=[O:27])[CH3:26])[CH:22]=1>C(O)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([O:28][CH3:29])=[C:21]([CH:23]2[CH2:3][C:2](=[O:1])[CH2:26][C:25](=[O:27])[CH2:24]2)[CH:22]=1

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 536609684-(5-Chloro-2-methoxyphenyl)-3-buten-2-one

生成物 1

HCID 183177015-(5-Chloro-2-methoxyphenyl)cyclohexane-1,3-dione

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 20% sodium ethoxide in ethanol (2.3 g) was added at room temperature diethyl malonate (5.4 g) and then was added little by little 4-(5-chloro-2-methoxyphenyl)-3-buten-2-one (6.8 g), and the reaction mixture was stirred at room temperature for 30 minutes, refluxed for 2 hours and cooled. The solvent was evaporated, and to the residue was added water. The aqueous layer was washed with ethyl acetate and concentrated. To the residue was added 2M sodium hydroxide (18 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (18 ml) for 15 minutes, and the mixture was refluxed for 15 minutes, cooled and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 5-(5-chloro-2-methoxyphenyl)cyclohexane-1,3-dione (7.3 g) as amorphous.

後処理

  1. temperaturerefluxed for 2 hours
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. additionto the residue was added water
  5. washThe aqueous layer was washed with ethyl acetate
  6. concentrationconcentrated
  7. additionTo the residue was added 2M sodium hydroxide (18 ml)
  8. temperaturethe mixture was refluxed for 2 hours
  9. temperaturecooled
  10. additionTo the mixture was added 2.5M sulfuric acid (18 ml) for 15 minutes
  11. temperaturethe mixture was refluxed for 15 minutes
  12. temperaturecooled
  13. extractionextracted with ethyl acetate
  14. washThe organic layer was washed with water and saturated brine
  15. dry with materialdried with magnesium sulfate
  16. customUnder reduced pressure, the solvent was evaporated

出典と根拠

ORDレコード
ord-3e99606bc58c448ab61e54d7e0e90cd2
出典データセット
uspto-grants-2002_02
特許番号
US06350749B1

反応ノート

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