Potassium Carbonate → 3-(3-Phenyl-propyl)-pentane-2,4-dione

HRID 1064545

반응식

HRID 1064545 반응식
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[C:8]1([CH2:14][CH2:15][CH2:16]I)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:8]1([CH2:14][CH2:15][CH2:16][CH:3]([C:2](=[O:7])[CH3:1])[C:4](=[O:6])[CH3:5])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 31261AcetylacetoneHCID 138121Benzene, (3-iodopropyl)-

생성물 1

HCID 221748543-(3-Phenyl-propyl)-pentane-2,4-dione수율 42%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A mixture of pentane-2,4-dione (3.87 g, 38.6 mmol), 3-phenyl-1-iodopropane (3.18 g, 12.9 mmol) and anhydrous potassium carbonate (1.7 g, 12.3 mmol) in acetone (7.5 mL) was heated to reflux for 24 hours. The room temperature reaction mixture was filtered, and the filter cake washed with acetone (25 mL×3). The combined filtrates were concentrated, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried (magnesium sulfate), and concentrated to an oil. Flash chromatography over silica (ethyl acetate/hexanes) afforded 1.13 g (42%) of a colorless oil. The proton spectrum in deuterochloroform showed the product exists as a mixture of keto and enol tautomers.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 24 hours
  3. customThe room temperature reaction mixture
  4. filtrationwas filtered
  5. washthe filter cake washed with acetone (25 mL×3)
  6. concentrationThe combined filtrates were concentrated
  7. customthe residue was partitioned between ethyl acetate and water
  8. washThe organic layer was washed with water and brine
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated to an oil

출처 및 근거

ORD 기록
ord-dd30148b0ff0469da9d627da54295a21
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06969728B2

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