Water → 2-(Tetrahydro-2-thienyl)pyridine

Participants

Reaction Steps

A solution of pyrid-2-ylmethyl 3-chloropropyl sulphide (330 g) in anhydrous tetrahydrofuran (400 cc) is added dropwise, in the course of 20 minutes, at a temperature of about 25° C., to a solution of potassium tert.-butylate (283 g) in a mixture of anhydrous hexamethylphosphorotriamide (428 cc) and anhydrous tetrahydrofuran (2300 cc). After stirring for 1 hour, the reaction mixture is added to a mixture of distilled water (4200 cc) and diethyl ether (2500 cc). After decantation, the aqueous phase is again extracted with diethyl ether (1700 cc). The combined ether extracts are washed three times with distilled water (12600 cc in total), dried over anhydrous sodium sulphate and concentrated to dryness. 2-(Pyrid-2-yl)-tetrahydrothiophene (189 g) is thus obtained in the form of a brown oil [Rf=0.56; chromatography on a thin layer of silica gel; solvent: ethyl acetate-cyclohexane (50:50 by volume)].

Provenance & Evidence