Thionyl Chloride → 5-Chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine

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A mixture of 2-(2-phenyl-4-thiazolylmethoxy)-5-pyridylmethanol (2.98 g) and thionyl chloride (15 ml) was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure and saturated aqueous sodium hydrogen carbonate was added to the residue. The mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and 5-chloromethyl-2-(2-phenyl-4-thiazolylmethoxy)pyridine (2.40 g, yield 76%) was obtained as colorless crystals from a fraction eluted with ethyl acetate. The crystals were recrystallized from tetrahydrofuran-hexane. melting point: 117–118° C.

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