Potassium Iodide → 6-Methanesulfonyloxy-2-(4-methanesulfonyloxyphenyl)-3-[4-(2-pyrrolidinoethoxy)benzoyl]benzo[b]thiophene, hydrochloride

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Reaction Steps

A 1.19 g. portion of the product of Example 30 above, 20 ml. of anhydrous dimethylformamide and 3.4 g. of freshly distilled pyrrolidine were added to a flask at 25°, and then 100 mg. of powdered potassium iodide was added and the mixture was stirred at ambient temperature for 1 hour. The mixture was then evaporated under vacuum, 25 ml. of saturated aqueous sodium bicarbonate was added, and the mixture was extracted twice with 25 ml. portions of ethyl acetate. The extract was washed five times with 20 ml. portions of aqueous sodium chloride, and was dried over magnesium sulfate and evaporated to a brown oil. The oil was dissolved in 25 ml. of hydrochloric acid in methanol, which had been prepared by addition of 10 ml. of acetyl chloride to 100 ml. of methanol under nitrogen at 0°. The mixture was then evaporated to dryness under vacuum, and the resulting foam was crystallized from denatured ethanol to provide 1.07 g. of crystals, m.p. 206°-207°.

Provenance & Evidence