Diethyl Malonate → 5-(2-Fluoro-5-methylphenyl)cyclohexane-1,3-dione

HRID 1700717ノート

反応式

HRID 1700717 の反応式
[O-:1][CH2:2][CH3:3].[Na+].C(OCC)(=O)CC(OCC)=O.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH:24]=[CH:25][C:26](=[O:28])[CH3:27]>C(O)C>[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[CH:24]1[CH2:3][C:2](=[O:1])[CH2:27][C:26](=[O:28])[CH2:25]1

参加物

5

反応物 3

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 539200784-(2-Fluoro-5-methylphenyl)-3-buten-2-one

生成物 1

HCID 183174315-(2-Fluoro-5-methylphenyl)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 (1.4 g) was added at room temperature diethyl malonate (3.3 g) and then was added little by little 4-(2-fluoro-5-methylphenyl)-3-buten-2-one (3.5 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 (11 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (11 ml) for 5 minutes, and the mixture was refluxed for 30 minutes and cooled. Precipitated crystals were filtered, washed with water and isopropylether to give 5-(2-fluoro-5-methylphenyl)cyclohexane-1,3-dione (1.6 g) as colorless crystals.

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 (11 ml)
  8. temperaturethe mixture was refluxed for 2 hours
  9. temperaturecooled
  10. additionTo the mixture was added 2.5M sulfuric acid (11 ml) for 5 minutes
  11. temperaturethe mixture was refluxed for 30 minutes
  12. temperaturecooled
  13. customPrecipitated crystals
  14. filtrationwere filtered
  15. washwashed with water and isopropylether

出典と根拠

ORDレコード
ord-389d8f72a2284b97b990a5c0af487823
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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