[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:13]=C/C3C=CC=CC=3)=[N:10][O:11][CH:12]=2)=[CH:4][CH:3]=1.[O:21]=[O+][O-].CSC>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([CH:13]=[O:21])=[N:10][O:11][CH:12]=2)=[CH:4][CH:3]=1(E)-4-(4-Chlorophenyl)-3-styrylisoxazole (2 g, 7.1 mmol) was dissolved in DCM/MeOH (20 mL/2 mL) and cooled to −78° C. The reaction was placed under ozonolysis conditions (O3 bubbling) until full disappearance of starting material. DMS (8 mL) was added and the reaction was let warm to ambient temperature. After 15 h, the reaction was partitioned between EtOAc and H2O. The organics were separated, washed with saturated aqueous NaHCO3, and dried with saturated aqueous NaCl. Solvents were removed in vacuo and the residue purified by column chromatography on silica to provide the desired product: MS (m/z) 208.0 [M+H]+.
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