To a stirred solution of the (E)-3-(7-chloro-2quinolinylethenyl)phenol (1.485 g, 5.28 mmol) in acetone (120 ml) and dimethylformamide (I5 ml) at room temperature are added successively potassium carbonate (1.09 g, 7.0 mmol) and 2-cyano-6-(bromomethyl)benzoxazole (1.25 g, 5.27 mmol). The resulting solution-suspension is refluxed for 16 hours and concentrated. Water (100 ml) and ethyl acetate (150 ml) are added. Extraction with ethyl acetate is followed by washing with water and brine, drying (MgSO4) and evaporation under reduced pressure. The residue is subjected to flash chromatography over silica gel. Elution is with 33% ethyl acetate in hexane and concentration of the appropriate fractions provides (E)-2-cyano-6-[3-(7-chloro-2-quinolinylethenyl) phenoxymethyl]-benzoxazole.
