Pyridine → HCID 60206954, compound

Participants

Reaction Steps

At 0° C., to a stirred solution of the hydroxy-isobutylbenzamide (3.72 g, 19.3 mmol) in pyridine (15 mL) under argon was added trifluoromethanesulfonic anhydride (10.2 ml, 57.8 mmol). The reaction mixture was eventually warmed up to room temperature and stirred overnight. The reaction was diluted with ethyl acetate, and washed with 1N HCl (×2), water (×1) and brine (×1), dried with sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by flash column chromatography (5% ethyl acetate: hexane) to afford 2.66 g of the desired product as a clear oil (50% yield). 1H NMR (CDCl3) δ 7.56 (s, 1 H), 7.50 (d, J=8 Hz, 1 H), 7.43 (d, J=8 Hz, 1 H), 2.57 (d, J=8 Hz, 2 H), 1.92 (m, 1 H), 0.97 (d, J=4 Hz, 6 H).

Provenance & Evidence