Dibutyltin oxide → HCID 178497606, compound

Participants

Reaction Steps

To a mixture consisting of {1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropyl}-acetonitrile (the synthetic intermediate prepared in Example 42, Step A, 0.7 g) in toluene (10 mL) are added di-n-butyltin oxide (0.48 g) and azidotrimethylsilane (0.51 mL.) The stirring mixture is brought to reflux and continued stirring overnight. The mixture is subsequently cooled to room temperature, diluted with ethyl acetate (40 mL), and sequentially washed with water (20 mL) and brine solution (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (1:1 v/v) and further elution with ethyl acetate afforded the synthetic intermediate 5-{1-[3-(4-methoxymethoxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropylmethyl}-1H-tetrazole (0.6 g.)

Provenance & Evidence