Sodium Iodide → HCID 12148452, compound

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Reaction Steps

In a 50 ml flask, equipped with a magnetic stirrer, 0.135 g of the tosylate compound of Example 12 was treated with an excess of sodium iodide (>10 equivalents) in 10 ml of acetone at reflux for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a separation funnel and 20 ml of ethyl acetate was added. The organic layer was washed with 20 ml of water, 20 ml of 0.5M aqueous Na2S2O3, and 20 ml of brine, dried (Na2SO4) and concentrated at reduced pressure. The crude product was purified by column chromatography (Merck 60 SiO2, eluens ethyl acetate/heptane=3/2) to give two fractions. The first fraction was the product as was determined by 1H-NMR spectroscopy. Isolated yield: 0.048 g (40%).

Provenance & Evidence