Tetrahydrofuran → 3-(3-Phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

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Reaction Steps

To a stirred mixture of 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (7A, 1.96 g, 4.80 mmol) and THF (20 mL) were added NMO (50% in water, 1.493 mL, 7.20 mmol) and osmium tetroxide (4% in water, 1.173 mL, 0.192 mmol) at room temperature. The mixture was vigorously stirred at room temperature overnight. A solution of sodium periodate (1.540 g, 7.20 mmol) in water (10 mL) was added. The mixture was stirred at room temperature under nitrogen for 30 min. Water (20 mL) was then added. The solid was filtered, washed with water (2×5 mL) and ethanol (2 mL) and dried to give 3-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (1.92 g, 4.68 mmol, 98%) as a white solid. The compound had an HPLC retention time=3.95 min (condition C); LC/MS M+1=410.9.

Provenance & Evidence