Sodium periodate → (5-Chloro-2-oxo-1,3-benzothiazol-3(2H)-yl)acetaldehyde

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Reaction Steps

5-chloro-3-(2-propen-1-yl)-1,3-benzothiazol-2(3H)-one (0.43 g, 1.9 mmol) (0.43 g, 1.9 mmole) was dissolved in 1,4-dioxane (20 ml) and water (22 ml) was added. Sodium periodate (0.94 g, 4.4 mmol) was added followed by 4% osmium tetroxide in water (2.1 ml) and stirred at rt for 30 mins after which time a heavy precipitate had formed. Water (20 ml) was added followed by more sodium periodate (1.9 g, 8.9 mmol) and the mixture stirred at rt for 18 h. The mixture was concentrated in-vacuo to a small volume and partitioned between water (50 ml) and DCM (2×50 ml). The organics were separated and dried. Chromatography on silica gel eluting with a gradient of 25-100% ethyl acetate/40-60 petroleum ether gave 0.21 g, 48%) of the title compound.

Provenance & Evidence