Sodium Iodide → HCID 13711329, compound

Participants

Reaction Steps

The compound 11 (2.0 g, 4.7 mmol) and dry N(C2H5)3 (1.13 g, 11.2 mmol) were stirred in dry acetone (60 ml) at room temperature for 30 minutes. The mixture was treated with ethyl 1-chloroethyl carbonate (1.70 g, 11.2 mmol) and NaI (1.67 g, 11.2 mmol) and heated under reflux for 23 hours. After completion of the reaction, the precipitate was removed, and the solvent was removed frcm the filtrate. The residue was extracted with benzene, washed with saturated aqueous solution of NaHCO3 and saturated solution of NaCl and dried over anhydrous Na2SO4 . The solvent was evaporated to give a colorless viscous product. The resultant product was dissolved in developing solvent and purified by silica gel column chromatography (developing solvent: benzene:ether=95:5) to give the desired compound as white solid (1.34 g, crude yield, 44%). The solid was dissolved in methanol at room temperature, treated with water, and cooled with a solution of dry ice in acetone. The precipitated solid was filtered by suction, followed immediately by drying under reduced pressure to give the desired compound as white crystal (970 mg, yield, 32%). m.p., 48°-51° C.

Provenance & Evidence