反应详情

Methyl 5-(3-chlorophenylthio)pyrrole-3-carboxylate (1.5 g.) was refluxed with 10 ml. of 1 N sodium hydroxide and 20 ml. of methanol, at which time thin layer chromatography (silica gel with hexane-5/ethyl acetate-1/5% acetic acid as eluant) indicated hydrolysis was complete. The methanol was allowed to evaporate. The aqueous residue was diluted with approximately one volume of water and extracted twice with ether. The aqueous phase was acidified with 6 N hydrochloric acid and product extracted multiply into ethyl acetate. The combined ethyl acetate extracts were back-washed with water and then with saturated brine, dried over anhydrous sodium sulfate and evaporated to an oil. Trituration of the oil with hexane gave 5-(3-chlorophenylthio)pyrrole-3-carboxylic acid (1.32 g., m.p. 134°-137° C., m/e 253).

1. customhydrolysis
2. customto evaporate
3. additionThe aqueous residue was diluted with approximately one volume of water
4. extractionextracted twice with ether
5. extractionextracted multiply into ethyl acetate
6. washThe combined ethyl acetate extracts were back-washed with water
7. dry with materialwith saturated brine, dried over anhydrous sodium sulfate
8. customevaporated to an oil