Water → 2-Methoxymethyloxy-3,4,5,6-tetramethoxybenzaldehyde
Reaktionsgleichung
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[C:6]=1[O:17][CH3:18].C([Li])CCC.CN([CH:27]=[O:28])C.O>CCOCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([O:17][CH3:18])=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[C:10]=1[CH:27]=[O:28]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
6.2 g of 1-methoxymethyloxy-2,3,4,5-tetramethoxybenzene prepared in Referential Example 13 was dissolved in 50 ml of anhydrous ether, and 18 ml of n-butyllithium (1.6M n-hexane solution) was dropwise added thereto at -20° C. while stirring. After the mixture was stirred at 0° C. for 30 min, the temperature was returned to -20° C. and 3.5 ml of DMF was dropwise added thereto. After 100 ml of water was added thereto, the mixture was extracted with ethyl acetate, and the organic phase was washed with water, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3) to prepare 5.6 g of the product compound as a light yellow oleaginous substance.
Aufarbeitung
- stirringAfter the mixture was stirred at 0° C. for 30 min
- customwas returned to -20° C.
- extractionthe mixture was extracted with ethyl acetate
- washthe organic phase was washed with water
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=7:3)
- customto prepare 5.6 g of the product compound as a light yellow oleaginous substance
Quellen und Nachweise
- ORD-Eintrag
- ord-73a55a75cb0f4a6b8754766dafcfa860
- Quelldatensatz
- uspto-grants-1995_01
- Patentnummer
- US05385942
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