[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([CH:11](O)[CH2:12][CH:13]([CH3:15])[CH3:14])=[C:8]([CH3:17])[C:7]=2[CH:18]=1.N1C=CC=CC=1.S(Cl)([Cl:27])=O.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Cl:27][CH:11]([C:9]1[O:10][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:18][C:7]=2[C:8]=1[CH3:17])[CH2:12][CH:13]([CH3:15])[CH3:14]To a solution (10 mL) of 1-(5-methoxy-3-methyl-1-benzofuran-2-yl)-3-methylbutan-1-ol (761 mg) synthesized above in toluene were added pyridine (297 μL) and thionyl chloride (268 μL), and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution was added to quench the reaction, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give the title object compound (769 mg, 94%) as a brown oil.
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