Chloromethyl Methyl Ether → 3-Methoxymethoxy-5-phenylisoxazole

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.

1. temperatureWhile the reaction mixture was cooled to 5° C.
2. stirringby stirring of the resulting mixture at the same temperature for one hour
3. extractionextracted with ether (200 ml×2)
4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
5. filtrationAfter filtration
6. customthe solvent was evaporated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

ORD record

ord-b458e4ab7e1543c9bd71a7188c679d5d

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06005116