Sodium Iodide → Ethyl 4-[5-(5-chloro-2-thienyl)-5-oxo-pentoxy]benzoate

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Reaction Steps

A mixture consisting of 2-chloro-5-(5-chloropentanoyl)thiophene (3c) (2.13 g, 0.009 mol), sodium iodide (1.1 g, 0.0073 mol), 4-hydroxyethylbenzoate (1.7 g, 0.010 mol), and anhydrous potassium carbonate (6.2 g, 0.045 mol) in acetonitrile (50 ml) was refluxed for 24 hrs., cooled, and filtered. The resulting solution was deprived of the solvent and the residue was taken up with dichloromethane (100 ml). After washing with water and subsequent drying on anydrous sodium sulfate the solution was evaporated to dryness. The resulting solid was crystallized via cyclohexane to pure 5c (2.5 g; 76%). M.p. 87°-89° C. Anal. (C18H19ClO4S).

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