[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21]([O:23]CC)=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].O.[OH-].[Li+]>CO>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([C:13]#[C:14][C:15]2[CH:20]=[C:19]([C:21]([OH:23])=[O:22])[CH:18]=[CH:17][N:16]=2)[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]Ethyl 2-(3,4,5-trimethoxyphenylethynyl)pyridine-4-carboxylate (1.40 g) was suspended in methanol (100 mL), to the suspension lithium hydroxide hydrate (189 mg) was added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue and the resultant mixture was neutralized with 1 M hydrochloric acid. After the reaction mixture was cooled with ice, crystals precipitated were collected by filtration to obtain the title compound as colorless crystals.
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