Hydrochloric Acid → 1-(3-Dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione

HRID 1613013ノート

反応式

HRID 1613013 の反応式
[H-].[Na+].[CH3:3][N:4]([CH3:16])[C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][CH:15]=1)[C:8]([O:10]CC)=O.[CH3:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].Cl>O1CCCC1>[CH3:16][N:4]([CH3:3])[C:5]1[CH:6]=[C:7]([C:8](=[O:10])[CH2:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[CH:14][CH:15]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6416PinacoloneHCID 24758Sodium hydrideHCID 12833325Ethyl 3-(dimethylamino)benzoate

生成物 1

HCID 189544861-(3-Dimethylaminophenyl)-4,4-dimethylpentane-1,3-dione収率 75%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Into a 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube, were charged 2.08 gm (31 mmol) of 60% sodium hydride and 5.0 gm (26 mmol) of ethyl 3-dimethylaminobenzoate. The mixture was dispersed in 40 ml of tetrahydrofuran and heated under refluxing. To the mixture was dropwise added 3.0 gm (30 mmol) of pinacolone and the mixture was heated with stirring for 3 hours. After cooling, 50 ml of 1N hydrochloric acid was added to the reaction mixture, and the organic layer was extracted twice with chloroform. The extract was thoroughly washed with water and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation to obtain an yellow oil. The oily substance was submitted to the Kugelrohr distillation at 200° C., 1 mmHg, and crystallized from hexane to give 4.81 gm (yield: 75%) of yellow solid product.

後処理

  1. customInto a 100 ml three-necked flask equipped with a stirrer, a dropping funnel, a reflux condenser, and a nitogen-inlet tube
  2. temperatureheated
  3. temperatureunder refluxing
  4. temperaturethe mixture was heated
  5. temperatureAfter cooling
  6. extractionthe organic layer was extracted twice with chloroform
  7. washThe extract was thoroughly washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was removed by evaporation
  10. customto obtain an yellow oil
  11. distillationThe oily substance was submitted to the Kugelrohr distillation at 200° C.
  12. custom1 mmHg, and crystallized from hexane

出典と根拠

ORDレコード
ord-7172cb5f5ef1430b98bd0c07da73f24d
出典データセット
uspto-grants-1993_03
特許番号
US05191121

反応ノート

読み込み中…