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

HRID 1064545

Reaction equation

HRID 1064545 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-dd30148b0ff0469da9d627da54295a21
Source dataset
uspto-grants-2005_11
Patent number
US06969728B2

Linked notes

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