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

HRID 1700715ノート

反応式

HRID 1700715 の反応式
[O-:1][CH2:2][CH3:3].[Na+].C(OCC)(=O)CC(OCC)=O.[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:28])=[C:21]([CH:23]=[CH:24][C:25](=[O:27])[CH3:26])[CH:22]=1>C(O)C>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH3:28])=[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 540396424-(5-Fluoro-2-methylphenyl)-3-buten-2-one

生成物 1

HCID 183177715-(5-Fluoro-2-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 (5.9 g) was added at room temperature diethyl malonate (14.0 g), and then added little by little 4-(5-fluoro-2-methylphenyl)-3-buten-2-one (13.4 g), and the mixture was stirred at room temperature for 30 minutes and then for 2 hours while heating, 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 (46 ml), and the mixture was refluxed for 2 hours and cooled. To the mixture was added 2.5M sulfuric acid (46 ml) for 10 minutes, and the mixture was refluxed for 30 minutes and cooled. Precipitated crystals were filtered and washed with water and isopropylether to give 5-(5-fluoro-2-methylphenyl)cyclohexane-1,3-dione (8.6 g) as colorless crystals.

後処理

  1. temperaturefor 2 hours while heating
  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 (46 ml)
  8. temperaturethe mixture was refluxed for 2 hours
  9. temperaturecooled
  10. additionTo the mixture was added 2.5M sulfuric acid (46 ml) for 10 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-0c7dbcbac66b43a3b27bae156f188401
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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