C(=S)=S.[CH2:4]([C:6]1[O:7][C:8]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:9]=2[CH:10]=1)[CH3:5].[C:17](Cl)(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1.[Sn](Cl)(Cl)(Cl)Cl>O>[C:17]([C:10]1[C:9]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:8]=2[O:7][C:6]=1[CH2:4][CH3:5])(=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=1Dried carbon disulfide solution (20 ml) of 2-ethyl-6-methoxy-benzofuran (2.76 g, 15.6 mmol) and p-anisoyl chloride (3.48 g, 20.3 mmol) was cooled on ice, to which tin chloride (IV) was dropped (5.25 g, 20.3 mmol) while stirring. The mixture was stirred at a temperature in a range of 5 to 10° C. for 3 hours and then poured into water. The organic layer was washed with diluted hydrochloric acid and water, dried over MgSO4, and concentrated under reduced pressure. Crude product thereof was purified by HPLC (silica gel, ethyl acetate: hexane=2:8) and a target product in pale yellow oily state (2.98 g, 9.60 mmol, 58%) was obtained.
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