Water → HCID 13720666, compound

Participants

Reaction Conditions

Reaction Steps

A solution of pyrid-4-yl-methyl 3-chloropropyl sulphide (81 g) in anhydrous tetrahydrofuran (100 cc) is added dropwise, in the course of 20 minutes and whilst keeping the temperature below 33° C., to a solution of potassium tert.-butoxide (69.5 g) in a mixture of anhydrous hexamethylphosphorotriamide (108 cc) and anhydrous tetrahydrofuran (560 cc). The reaction mixture is then stirred for 1 hour 30 minutes at a temperature of about 20° C.; it is then run into a mixture of distilled water (1000 cc) and diethyl ether (600 cc). After decantation, the aqueous phase is extracted twice with diethyl ether (400 cc in total). The ether extracts are combined, washed three times with distilled water (3000 cc in total), dried over anhydrous sodium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. 2-(Pyrid-4-yl)-tetrahydrothiophen (46.7 g) is thus obtained in the form of a brown oil.

Provenance & Evidence