Methyl (methylsulfinyl)methyl sulfide → 4-Tert-butyl-2-[5-{2-[2-methylsulfinyl-2-methylthioethenyl)phenylmethoxy}benzofuran-2-yl]thiazole

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A mixture of 4-tert-butyl-2-[5-(2-formylphenylmethoxy)benzofuran-2-yl]thiazole (0.61 g), methyl methylsulfinylmethyl sulfide (0.46 g) and triton B (phase transfer) (0.7 g) in tetrahydrofuran (3 ml) was stirred under reflux for 5 hours. After being cooled, the resulting mixture was poured into ice-water and extracted with ethyl acetate. The organic layer was washed with diluted aqueous hydrochloric acid and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to column chromatography on silica gel and eluted with a mixture of ethyl acetate and chloroform (1:5). The fractions containing object compound were combined and concentrated in reduced pressure to give a syrup of 4-tert-butyl-2-[5-{2-[2-methylsulfinyl-2-methylthioethenyl)phenylmethoxy}benzofuran-2-yl]thiazole (0.25 g).

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