Sodium Iodide → HCID 86750309, compound

Participants

Reaction Steps

NaI (1.135 g, 8.00 mmol) and Me3SiCl (1 mL, 8.0 mmol) were stirred in CH3CN (70 mL) at 0° C. Tris(8-dimethylaminocarbonylthio-2,2,6,6-tetramethylbenzo-[1,2-d:4,5-d']bis(1,3)-dioxole-4-yl)methanol (1.00 g, 0.9979 mmol (Example 43)) dissolved in CH3CN 10 mL) was added and the resulting solution stirred for 30 minutes when 1H NMR analysis of a small sample showed conversion to be complete. Na2S2O3 (sat., 30 mL) was added and the two phase system was stirred 30 minutes when more Na2S2O3 (sat. 30 mL) was added and the stirring was continued for 5 more minutes. The phases were separated and the organic layer was dried (MgSO4), filtered, the filter washed with diethyl ether (30 mL) and the solution was evaporated, yielding 1.16 g yellow to brown crystals. The crystals were dissolved in CH2Cl2, the solution was washed with NaHCO3 (30 mL, sat.) and H2O (30 mL), dried (MgSO4) and evaporated yielding 0.92 g of the pure title compound.

Provenance & Evidence