Hydrochloric Acid → HCID 178501816, compound

Participants

Reaction Steps

To a stirred solution of sodium t-butoxide (4.49 g, 45.3 mmol) in anhydrous THF (230 ml) was added dimethyl oxalate (5.41 g, 45.3 mmol) in anhydrous THF (60 ml) under argon condition. The mixture was stirred at room temperature for 30 min and a solution of 3-acetyl-5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)pyridin-2(1H)-one 6 (4.21 g, 11.3 mmol) in THF (60 ml) was added. The reaction mixture was stirred at room temperature for 3 h and then cooled in ice bath, and then 1N HCl (230 ml) was added in one portion. The crude product was extracted with ethyl acetate (2×230 ml). The combined organic layers were washed with saturated brine (2×230 ml) and ethyl acetate was distilled off to give a brown residue, which was triturated with methanol. The product was obtained by vacuum filtration. Yield 2.59 g (50%). 1H NMR (CDCl3, 500 MHz): δ 8.18 (d, 1H, J=3.1 Hz), 7.89 (s, 1H), 7.53 (s, 1H), 7.49-7.46 (s, 1H), 7.35-7.31 (s, 1H), 7.16-7.07 (m, 3H), 6.87-6.80 (m, 2H), 5.20 (s, 2H), 3.90 (s, 3H), 3.75 (s, 2H). 13C NMR (CDCl3, 125 MHz): δ 185.0, 171.9, 162.8, 162.6, 162.2, 160.6, 160.2, 159.6, 144.8, 142.0, 131.7, 131.2, 130.6, 124.8, 123.6, 122.4, 121.9, 117.7, 115.7, 111.7, 104.3, 101.8, 53.2, 47.6, 30.6.

Provenance & Evidence