Sodium periodate → HCID 86669893, compound

Participants

Reaction Steps

To a stirred solution of 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-7-vinyl-4,5-dihydronaphtho[2,1-d]oxazole (Preparation 48B, 26.2 mg, 0.064 mmol) in 0.5 mL of THF were added 0.113 mL of 10% N-methyl-morpholine-1-oxide in water and 0.04 mL of 4% OsO4 in water, and 0.2 mL of water. The heterogeneous mixture was stirred at room temperature for 18 hrs. To the homogenous reaction mixture was added 0.14 mL of 10% sodium periodate in water, and the mixture was stirred for 3 hrs. The reaction mixture was extracted with EtOAc, washed with water, brine dried over Na2SO4 and evaporated to give a solid residue which was purified by Combiflash (24 g silica gel) eluting with 1:9 followed by 3:7 EtOAc-hexane to give 2-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-4,5-dihydronaphtho[2,1-d]oxazole-7-carbaldehyde (20.2 mg, 77% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.69 (1H, s), 7.51-7.61 (2H, m), 7.44 (1H, d, J=7.70 Hz), 7.36 (2H, d, J=7.70 Hz), 7.22-7.30 (3H, m), 2.99-3.05 (2H, m), 2.83 (2H, t, J=8.03 Hz).

Provenance & Evidence