Sodium hydride → Methyl 3-[(4-chlorophenyl)carbonyl]-4-oxopentanoate
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:13])[CH2:9][C:10](=[O:12])[CH3:11])=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:17][C:18]([O:20][CH3:21])=[O:19]>CS(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([CH:9]([C:10](=[O:12])[CH3:11])[CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:13])=[CH:6][CH:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 20 °C
Versuchsvorschrift
A solution of 10 g (51 mmol) of 1-(4-chlorophenyl)butane-1,3-dione (commercially available) dissolved in dimethyl sulfoxide was slowly added dropwise to 2.237 g (56 mmol) of sodium hydride in 200 ml of dimethyl sulfoxide such that the temperature did not exceed 30° C. The mixture was stirred at 20° C. for another 30 minutes. 8.558 g (56 mmol) of methyl bromoacetate in a little dimethyl sulfoxide were then slowly added dropwise at 0° C. The mixture was stirred at 20° C. for 4 hours. The reaction mixture was poured into ice-water and extracted with dichloromethane. The organic phase was washed repeatedly with water. Drying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue gave 7.750 g of product (56.7% of theory).
Aufarbeitung
- customdid not exceed 30° C
- stirringThe mixture was stirred at 20° C. for 4 hours
- extractionextracted with dichloromethane
- washThe organic phase was washed repeatedly with water
- customDrying of the combined organic phases, removal of the solvent under reduced pressure and chromatography of the residue
Quellen und Nachweise
- ORD-Eintrag
- ord-104a49fee9a64c78b2c2388bdd603420
- Quelldatensatz
- uspto-grants-2012_10
- Patentnummer
- US08298994B2
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