Ammonium Chloride → 1-(4-Methoxy-6-methylpyridin-2-yl)propan-2-one
Reaktionsgleichung
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH3:10])[CH:4]=1.C([Li])CCC.CN(C)[C:18](=[O:20])[CH3:19].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[N:6]=[C:5]([CH2:10][C:18](=[O:20])[CH3:19])[CH:4]=1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 4-methoxy-2,6-dimethylpyridine (1.56 g) in tetrahydrofuran (15 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 9.1 ml) dropwise at −50° C. under a nitrogen atmosphere, and the mixture was warmed to 0° C. The mixture was cooled to −50° C., and N,N-dimethylacetamide (1.59 ml) was added dropwise. Then the mixture was warmed to room temperature, poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate (100 ml×2). The combined organic layer was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=2:1) to give 1-(4-methoxy-6-methylpyridin-2-yl)propan-2-one (1.75 g).
Aufarbeitung
- temperatureThe mixture was cooled to −50° C.
- temperatureThen the mixture was warmed to room temperature
- extractionextracted with ethyl acetate (100 ml×2)
- washThe combined organic layer was washed with brine
- dry with materialdried over sodium sulfate
- customevaporated under reduced pressure
- customThe residue was purified by column chromatography (silica gel 100 g, n-hexane:ethyl acetate=2:1)
Quellen und Nachweise
- ORD-Eintrag
- ord-5b93b648ca8a46579800173fe47cd2cd
- Quelldatensatz
- uspto-grants-2003_02
- Patentnummer
- US06521643B1
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