Reaktion #700104

Reaktionsgleichung

sodium methoxide

3-Hydroxy-5-phenylisoxazole

chloromethyl methyl ether

→

title compound

Ausbeute 61.5%

3-Methoxymethoxy-5-phenylisoxazole

Ausbeute 61.5%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturWhile the reaction mixture was cooled to 5° C.
2. 2
   workup.STIRRINGby stirring of the resulting mixture at the same temperature for one hour
3. 3
   Extraktionextracted with ether (200 ml×2)
4. 4
   Trocknenthe organic layer was dried over anhydrous magnesium sulfate
5. 5
   FiltrationAfter filtration
6. 6
   Sonstigethe solvent was evaporated under reduced pressure
7. 7
   SonstigeThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

Vorschrift

3-Hydroxy-5-phenylisoxazole (8.05 g) was dissolved in dimethylformamide (80 ml), and sodium methoxide (28% methanol solution, 3.24 g) was added dropwise thereto, followed by stirring of the resulting mixture at room temperature for one hour. While the reaction mixture was cooled to 5° C., chloromethyl methyl ether (4.83 g) was added thereto, followed by stirring of the resulting mixture at the same temperature for one hour. The reaction mixture was poured into ice-cold water (200 ml) and extracted with ether (200 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the title compound (6.30 g, 61%) as a colorless oil.

Quelle