Toluene → HCID 25241750, compound

Participants

Reaction Steps

38.63 g (0.28 mol) of zinc chloride are heated until molten under an argon atmosphere in a reactor. After cooling the reaction mass, 800 ml of toluene, 800 ml of acetonitrile and 44 g of 4 Å molecular sieve are added. The reaction mixture is stirred at ambient temperature for 90 minutes and 25 g (0.113 mol) of 3-iodophenol are added. The reaction mixture is brought to 90° C. and, after 2 minutes, 39 ml (0.28 mol) of triethylamine and 44.39 g (0.12 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide are added. The reaction mixture is kept stirred at 80° C. for 30 minutes. After cooling, water and ethyl acetate are added and the insoluble compounds are removed by filtration. The organic phase is washed successively with water, a 1N sodium hydroxide solution and a saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, decolored using active charcoal, filtered and evaporated under reduced pressure. The residue is purified by chromatography on a silica column, elution being carried out using a cyclohexane/ethyl acetate mixture (70/30; v/v), and recrystallized from isopropanol. The expected product is obtained in the form of a white powder with a yield of 37%.

Provenance & Evidence