[F:1][C:2]([F:17])([F:16])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=C)=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5].CC([OH:22])(C)C>O1CCOCC1.O.O=[Os](=O)(=O)=O>[F:1][C:2]([F:17])([F:16])[CH:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:22])=[CH:10][CH:9]=1)[C:4]([F:7])([F:6])[F:5]1-(2,2,2-Trifluoro-1-trifluoromethyl-ethyl)-4-vinyl-benzene (80 mg, 0.3 mmol) was dissolved in dioxane (6 ml) and water (5 ml). NaIO4 (181 mg, 0.84 mmol) and OsO4 (0.18 ml of a 2.5 % t-BuOH solution) were added. The mixture was allowed to stir at room temperature for 2 h, and then it was partitioned between ethyl acetate and brine. The ethyl acetate was washed with three additional times with brine, dried over MgSO4, and the solvent was removed under vacuum to give the title product (47 mg (61%), 0.18 mmol). 1H NMR (CDCl3): δ=10.08 (s, 1H), 8.04 (d, J=8.3 Hz, 2H), 7.76 (d, J=8.3 Hz, 2H), 5.82 (m, 1H).
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