Iodine → HCID 70819181, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4 (100 mg, 4.52 mmol) in acetonitrile (25 mL) was added ceric ammonium nitrate (0.248 g, 0.45 mmol) followed by iodine (0.631 g, 4.97 mmol). The mixture was stirred at 70° C. under nitrogen for 7 h. After completion of the reaction, the mixture was cooled to room temperature and treated with an ice-cold aqueous solution of sodium thiosulfate with stirring. The mixture was extracted with portions of ethyl ether. The combined organic phase was dried over anhydrous MgSO4 and concentrated under diminished pressure to afford a crude residue. The residue was purified by chromatography on a silica gel column. Elution with hexane/ethyl acetate gave 3-hexadecyl-5-iodo-2,6-dimethylpyridin-4(1H)-one (6) as a light yellow solid: yield 93 mg (68%); silica gel TLC Rf 0.60 (1:1 hexane/ethyl acetate); 1H NMR (400 MHz, CDCl3) δ 0.86-0.89 (m, 3H), 1.24-1.28 (m, 28H), 2.20 (s, 3H), 2.26 (s, 3H) and 2.32-2.39 (m, 2H).

Provenance & Evidence