[CH3:1][N:2]([CH2:10][C:11]#[CH:12])[C:3]1[S:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][N:2]([CH2:10][C:11]#[CH:12])[C:3]1[S:4][CH:5]=[C:6]([CH:8]=[O:9])[N:7]=12-(N-Methyl-2-propynylamino)-4-hydroxymethylthiazole (i) (4.36 g) was dissolved in methylene chloride (20 ml) and manganese dioxide (10 g) was added thereto. The mixture was stirred at room temperature for 16 hours and filtered off. The filtrate was evaporated and the residue was applied to column chromatography on silica gel (50 g) to give 2-(N-methyl-2-propynylamino)-4-formylthiazole (j) (2.56 g, yield 59%) from chloroform-ether (3:1) eluate as an oil.
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