Cl[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:11]=2[C:12]=1[CH3:13])=[O:7].CO.O1CCCC1.[CH3:27][S-:28].[Na+]>O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:10]2[O:9][C:8]([C:6](=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2][S:28][CH3:27])=[C:12]([CH3:13])[C:11]=2[CH:14]=1To a mixture of 5-chloro-1-(5-methoxy-3-methyl-1-benzofuran-2-yl)pentan-1-one (1.30 g) synthesized above, methanol (15 mL) and tetrahydrofuran (15 mL) was added a 15% aqueous solution (4.33 mL) of sodium methanethiolate, and the mixture was stirred at room temperature for 1 hr and at 50° C. for 1 hr. Sodium methanethiolate (325 mg) was additionally added and the mixture was stirred at 50° C. for 1 hr. Sodium methanethiolate (325 mg) was additionally added again, and the mixture was stirred at 50° C. for 1 hr. Water 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. The residue was washed with hexane to give the title object compound (492 mg, 36%) as a yellow solid.
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