[CH2:1]([C:4]1[CH:12]=[CH:11][C:7]2=[N:8][O:9][N:10]=[C:6]2[CH:5]=1)[CH:2]=C.CO.C[N+]1([O-])CC[O:19]CC1.I([O-])(=O)(=O)=O.[Na+]>O.C1COCC1>[N:8]1[O:9][N:10]=[C:6]2[CH:5]=[C:4]([CH2:1][CH:2]=[O:19])[CH:12]=[CH:11][C:7]=12To a solution of 5-Allyl-2,1,3-benzoxadiazole (4.1 g, 26 mmol) in a solution of MeOH (30 mL), THF (50 mL), and water (20 mL) was added Osium Tetraoxide (6.0 mL 4% aq. solution, 0.77 mmol) and NMO (4.5 g, 38 mmol). The mixture was allowed to stir at 25° C. for 16 hours. TLC showed complete reaction. The reaction was diluted with water (200 mL) and extracted with EtOAc (200 mL×2). The extractions were combined, washed with brine, dried over sodium sulfate, and concentrated. The resulting product was redissolved in water and methanol (50 mL each), and cooled to 0° C. To that solution was added an aqueous solution of sodium periodate (7.2 g, 33 mmol). TLC showed complete reaction within 15 minutes. The reaction was diluted with water (100 mL) and extracted with EtOAc (100 mL×2). The extractions were combined, washed with brine, dried over sodium sulfate, and concentrated to obtain the product which was used in the next step without further purification.
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