Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.C([Li])CCC.CN(C)[C:17](=[O:19])[CH3:18].[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([CH2:1][C:17](=[O:19])[CH3:18])[CH:7]=1Komponenten
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 2-methyl-4-methoxypyridine (2.03 g) in tetrahydrofuran (20 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 12.1 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 (1.99 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=1:2) to give 1-(4-methoxypyridin-2-yl)propan-2-one (2.35 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=1:2)
Quellen und Nachweise
- ORD-Eintrag
- ord-0c8a7b8361f841a183aec70d59e1bb57
- Quelldatensatz
- uspto-grants-2003_02
- Patentnummer
- US06521643B1
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