Sodium periodate → HCID 178458858, compound

Participants

Reaction Steps

To a solution of 5.5 g (0.0143 mol) of 2-propionyl-3-hydroxy-5-(6-(4-(methylthio)phenoxy)-2-pyridyl)cyclohex-2-en-1-one in 250 mL of methanol was added a solution of 3.22 g (0.0151 mol) of sodium periodate in 25 mL of water. The resulting mixture was stirred at ambient temperature for 24 hours and the sodium iodate by-product was filtered off. The filtrate was reduced in vacuo and the residue dissolved in 150 mL of CH2Cl2 and washed with water (3×150 mL) and dried over Na2SO4 and the solvent removed in vacuo. The crude product was dissolved in CH2Cl2 and placed on a column of silica gel. The column was initially eluted with CH2Cl2 and then with a 90:10 CH2Cl2 :acetone mixture. The product fractions were combined and the solvent removed in vacuo giving the above named product in a yield of 3.2 g (56 percent of theoretical). The product melted at 78°-86° C.: Rf -0.24 (silica gel, 5:95 methanolCH2Cl2), 1H NMR (CDCl3) δ1.1 (t, 3H, CH3CH2 --), 2.5-3.6 (m, 7H, ring protons and CH3CH2 --), 2.72 (s, 3H, CH3S(O)--), 6.7-7.8 (m, 7H, ArH), 18.0 (s, 1H, OH).

Provenance & Evidence