[CH3:1][NH:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10].C([Li])(CC)C.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[CH:22]=[O:23].O>O1CCCC1.C1CCCCC1.C(OCC)(=O)C>[CH3:1][NH:2][C:3](=[O:11])[C:4]1[C:9]([CH:22]([OH:23])[C:21]2[CH:20]=[C:19]([O:18][CH3:17])[C:26]([O:27][CH3:28])=[C:25]([O:29][CH3:30])[CH:24]=2)=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:10]
A solution of N-methyl-2-chlorobenzamide (13.0 g) in tetrahydrofuran (300 ml) is cooled to −70° C., and thereto is added dropwise a 1.3M solution of sec-butyl lithium in cyclohexane (130 ml) over a period of 20 minutes. The mixture is stirred at −60° C. for 30 minutes, and thereto is added dropwise a solution of 3,4,5-trimethoxybenzaldehyde (15.0 g) in tetrahydrofuran (100 ml) over a period of 10 minutes. The mixture is stirred at the same temperature for one hour, and thereto are added water and ethyl acetate (300 ml). The ethyl acetate layer is separated, washed, dried, and concentrated under reduced pressure. The residue is crystallized from diethyl ether to give N-methyl-2-chloro-6-[hydroxy-(3,4,5-trimethoxyphenyl)methyl]benzamide (19.2 g) as listed in Table 54.
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