N-Fluorobenzenesulfonimide → 4-Fluoro-3-methoxymethoxy-5-phenylisoxazole

Temperature

-78 °C

3-Methoxymethoxy-5-phenylisoxazole (2.05 g) was dissolved in anhydrous tetrahydrofuran (30 ml), and the solution was cooled to -78° C. Butyllithium (1.68M hexane solution, 7.1 ml) was added dropwise thereto, and the resulting mixture was stirred at the same temperature for 15 minutes. Then, N-fluorobenzenesulfonimide (3.15 g) was added to the reaction mixture, followed by stirring of the resulting mixture at the same temperature for 15 minutes. The cooling bath was removed and the temperature of the resulting mixture was raised to room temperature. The reaction mixture was poured into ice-cold water (200 ml) and extracted with ether (200 ml×2). 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 (1.78 g, 80%) as a colorless oil.

1. stirringby stirring of the resulting mixture at the same temperature for 15 minutes
2. customThe cooling bath was removed
3. temperaturethe temperature of the resulting mixture was raised to room temperature
4. additionThe reaction mixture was poured into ice-cold water (200 ml)
5. extractionextracted with ether (200 ml×2)
6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
7. filtrationAfter filtration
8. customthe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1)

ORD record

ord-968d31f437b147b18708bace648da188

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06005116