Trichloroisocyanuric Acid → HCID 67172499, compound

Participants

Reaction Steps

To methyl 2-hydroxy-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetate (Preparation 134A, 260 mg, 0.55 mmol) in dichloromethane (5 mL) was added 1,3,5-trichloro-1,3,5-triazinane-2,4,6-trione (193 mg, 0.83 mmol). The reaction mixture was stirred for 5 min. at room temperature. The reaction mixture was cooled to 0° C. and TEMPO (12.95 mg, 0.083 mmol) was added. The reaction mixture was warmed up to room temperature and was stirred for 1 h. The layers were separated and the organic phase was washed with sat. aq. sodium bicarbonate (5 mL) followed by 1N hydrochloric acid (5 mL) and brine (5 mL). The organic layer was dried and concentrated to provide methyl 2-oxo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)acetate (250 mg, 0.53 mmol, 97% yield): LC/MS M+1=470.02; 1H NMR (400 MHz, CDCl3) δ ppm 8.16-8.22 (1H, m), 8.01-8.08 (2H, m), 7.77 (2H, d, J=7.48 Hz), 7.53-7.68 (3H, m), 4.03 (3H, s), 3.15 (4H, s).

Provenance & Evidence