Sodium Thiosulfate → 3-cyano-N-[2-(4-cyanophenyl)-4-oxobutyl]-N-methyl-1-naphthamide

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Reaction Steps

3-Cyano-N-[2-(4-cyanophenyl)-4-hydroxybutyl]-N-methyl-1-naphthamide (0.70 g, 1.8 mmol) was dissolved in CH2Cl2 (15 mL) and to the resultant solution was added Dess Martin Periodinane (0.85 g, 2.0 mmol) in portions. The mixture was stirred at room temperature overnight and then sodium thiosulfate (1.9 g, 12 mmol), dissolved in saturated NaHCO3 solution (30 mL), was added. The mixture was stirred vigorously for 2 h and then the organic solution was washed with brine and dried over Na2SO4. The solvent was removed by evaporation and the residue purified by flash chromatography (ethyl acetate-heptane, 4:1). There was obtained 0.50 g, (43%) of 3-cyano-N-[2-(4-cyanophenyl)-4-oxobutyl]-N-methyl-1-naphthamide as a white solid. 1H NMR (400 MHz, CDCl3): 2.7 (s, 3H), 2.9-4.4 (cm, 5H), 6.4-7.8 (cm, 8H), 7.9 (d, 1H), 8.2 (s, 1H), 9.8 (s, 1H); LCMS: m/z 382 (M+1)+.

Provenance & Evidence