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

HRID 1613013노트

반응식

HRID 1613013 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-7172cb5f5ef1430b98bd0c07da73f24d
출처 데이터셋
uspto-grants-1993_03
특허 번호
US05191121

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