Reaktionsgleichung
[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]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
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.
Aufarbeitung
- temperaturewas heated
- temperatureto reflux for 24 hours
- customThe room temperature reaction mixture
- filtrationwas filtered
- washthe filter cake washed with acetone (25 mL×3)
- concentrationThe combined filtrates were concentrated
- customthe residue was partitioned between ethyl acetate and water
- washThe organic layer was washed with water and brine
- dry with materialdried (magnesium sulfate)
- concentrationconcentrated to an oil
Quellen und Nachweise
- ORD-Eintrag
- ord-dd30148b0ff0469da9d627da54295a21
- Quelldatensatz
- uspto-grants-2005_11
- Patentnummer
- US06969728B2
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