Acetyl chloride → 5-(4-Acetoxyphenyl)-3-(2-(N-tert-butoxycarbonylamino)ethoxy)isoxazole

Participants

Reaction Steps

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-5-(4-hydroxyphenyl)isoxazole (0.15 g) was dissolved in tetrahydrofuran (1.5 ml), and triethylamine (0.07 ml) and acetyl chloride (0.04 ml) were added dropwise thereto at 5° C. under a nitrogen atmosphere, followed by stirring of the resulting mixture at room temperature for 30 minutes. The reaction mixture was poured into ice-cold water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and 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=2/1) to obtain the title compound (0.12 g, 71%) as a colorless powder.

Provenance & Evidence