3-phenyl-5-(4-methyl-beta-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide → N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide

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Reaction Steps

A mixture of 41.4 g. (0.123 mole) of 3-phenyl-5-(4-methyl-β-hydroxyphenethyl)-N-methyl-isoxazole-4-carboxamide and 800 ml. of acetone is treated dropwise with the addition of 92.5 ml. (0.185 mole) of Jones reagent [100 g. chromium trioxide, 160 ml. concentrated sulfuric acid with water to 500 ml.] and the resulting mixture is stirred at room temperature for 2 hours. The supernatant liquid is decanted and the solvent removed in vacuo, the residue is taken up in water/methylene chloride and the layers separated. The organic phase is washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue is treated with ether to give a solid and then triturated with ethanol to give N-methyl-5-(4-methylphenacyl)-3-phenyl-4-isoxazole carboxamide.

Provenance & Evidence