反应详情

A solution of N-(6-methoxy-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-3-phenyl-4-(trifluoromethyl)isoxazole-5-carboxamide (Preparation 43A, 135.6 mg, 0.315 mmol) and phosphorous oxychloride (1.468 mL, 15.75 mmol) in anhydrous dichloroethane (5 mL) was heated under an argon atmosphere at 85° C. for 13 hrs. The solvent and excess phosphorous oxychloride were evaporated off and the residue was purified by Combiflash (12 g silica gel) eluting with 2:8 ethyl acetate-hexane to give the desired 7-methoxy-2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazole (126 mg, 97% yield) as an oil. 1H NMR (400 MHz, MeOD) δ ppm 7.62-7.66 (2H, m), 7.53-7.60 (3H, m), 7.48 (1H, d, J=8.14 Hz), 6.94 (1H, d, J=2.20 Hz), 6.89-6.93 (1H, m), 3.84 (3H, s), 3.18 (2H, t, J=8.03 Hz), 2.95-3.01 (2H, m).

1. customThe solvent and excess phosphorous oxychloride were evaporated off
2. customthe residue was purified by Combiflash (12 g silica gel)
3. washeluting with 2:8 ethyl acetate-hexane