Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]([C:10]2[O:11][CH2:12][C:13]([CH3:16])([CH3:15])[N:14]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1C[O:20][CH2:19]C1.C([Li])CCC.CN(C=O)C>O.CCCCCC>[CH3:15][C:13]1([CH3:16])[CH2:12][O:11][C:10]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH3:9])=[C:2]([CH:3]=2)[CH:19]=[O:20])=[N:14]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
2-(3-Bromo-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydrooxazole (2.1 g, 7.4 mmol) and THF (15 ml) were mixed, and this solution was cooled to -78° C. A hexane solution (1.6M, 4.75 ml) of n-butyllithium (7.6 mmol) was added, and the mixture was stirred for 2 hours. DMF (1.16 ml, 15 mmol) was added and the mixture was stirred for 20 minutes. Water (20 ml) was added to stop the reaction. The aqueous layer was extracted twice with ethyl acetate (20 ml). The organic layers were combined, and washed with saturated brine (30 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3) to give 5-(4,4-dimethyl-4,5-dihydrooxazole-2-yl)-2-methoxybenzaldehyde (0.71 g, 41%) as colorless transparent crystals.
Aufarbeitung
- stirringthe mixture was stirred for 20 minutes
- customthe reaction
- extractionThe aqueous layer was extracted twice with ethyl acetate (20 ml)
- washwashed with saturated brine (30 ml)
- dry with materialThis solution was dried over anhydrous magnesium sulfate
- filtrationthe drying agent was filtered off
- concentrationThe filtrate was concentrated under reduced pressure
- customthe obtained residue was purified by column chromatography (hexane/ethyl acetate=3/1-1/3)
Quellen und Nachweise
- ORD-Eintrag
- ord-3e10c1049cdb44eab19e34cb31cf7c73
- Quelldatensatz
- uspto-grants-2000_01
- Patentnummer
- US06017919
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