Triacetoxyperiodinane → 2-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamide

Participants

Reaction Steps

under an N2 atmosphere, 2-chloro-N-(4-(((2-hydroxy-2-phenylethyl)amino)carbonyl)phenyl)benzamide (0.578 g, 1.46 mmol) was dissolved in DMF (7.00 ml). Dess-Martin periodinane (0.745 g, 1.76 mmol) was added and the reaction was stirred at room temperature for 3 hours. The reaction was diluted with ethyl acetate and a saturated aqueous solution of sodium bisulfate. The layers were separated and the organic layer was washed with water and brine. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was triturated with ethyl acetate and hexanes. The resulting solid was collected by filtration. The solid was suspended in pyridine (8.00 ml) and POCl3 (4.00 ml). The reaction was heated to 70° C. for 3 hours. The reaction was poured into a cooled 5% NaHCO3 solution and stirred vigorously for 15 minutes. The mixture was then extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by column chromatography eluting with 25% to 50% ethyl acetate in hexanes. The resulting solid was triturated with ethyl acetate/hexanes and collected by filtration to afford 2-chloro-N-(4-(5-phenyloxazol-2-yl)phenyl)benzamide (0.920 g, 16.8%). ESI m/z=375.0 (M+H+).

Provenance & Evidence