Triacetoxyperiodinane → 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazole-7-carbaldehyde

Participants

Reaction Steps

To a solution of (3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazol-7-yl)methanol (Preparation 60H, 0.027 g, 0.065 mmol) in dichloromethane (2.0 mL) at room temperature was added Dess-Martin Periodinane (0.030 g, 0.072 mmol). The reaction mixture was stirred for 30 min. The reaction was quenched with a 1:1 mixture of saturated aqueous sodium thiosulfate and saturated aqueous sodium bicarbonate (˜2.0 mL), extracted with dichloromethane (2×), and the combined organic layers were dried over anhydrous sodium sulfate and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure to afford 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4H-chromeno[3,4-d]isoxazole-7-carbaldehyde (0.027 g, 0.065 mmol, 100% yield) as a white solid. The product had an HPLC ret. time=3.31 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA.

Provenance & Evidence