Sodium periodate → Methyl 3-(4-(3-acetyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate

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Reaction Steps

To a stirred solution of methyl 3-(4-(3-(prop-1-en-2-yl)-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (Reference Example 49, 0.175 g, 0.516 mmol), and osmium tetroxide solution (0.21 g, 4 wt % in water, 0.033 mmol) in acetone (10.0 mL) and water (3.0 mL) was added sodium periodate (0.331 g, 1.55 mmol) at room temperature and the mixture was stirred at room temperature for 2 h. After this time, the reaction mixture was diluted with ethyl acetate, washed with water and saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The resultant residue was purified by flash column chromatography (silica gel, hexanes/ethyl acetate 9:1) to provide methyl 3-(4-(3-acetyl-5-(trifluoromethyl)phenyl)oxazol-2-yl)propanoate (0.128 g, 73%) as a white solid: ESI MS m/z 342 [M+H]+.

Provenance & Evidence