Water → 2,3,4,5-Tetraiodopyrrol-1-acetic acid

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Reaction Steps

TO a solution of 23.2 g of compound B), 2,3,4,5-tetraiodopyrrol-1-acetic acid ethyl ester (35.32 mmol) , in 840 mL of a dioxane (750 mL) / H2O (90 mL) mixture, 36 mL of 1M NaOH (36 mmol) are quickly added (10 min) and the final solution is kept at room temperature for 4 h. The reaction mixture is treated with carbon Carbopuron 4N, filtered, then acidified with 37% HC1 (w/w) and diluted in 500 1 of H2O, to give a solid which is filtered and purified by chromatography (silica gel (product E. Merck item 9385): eluent: CHCl3 : MeOH : 25% NH4OH (w/w) =7.5:2:0.3 (v/v/v)). Fractions with similar purity are collected, evaporated and diluted with 200 mL of H2O. By acidifying the aqueous phase with 40 mL of 1M HCl , a solid precipitates, which is filtered, washed with H2O and dried under reduced pressure. 21.5 g of 2,3,4,5-tetraiodopyrrol-1-acetic acid(34.20 mmol) are obtained.

Provenance & Evidence