Sodium Thiosulfate → 3-(1H-Benzimidazol-1-yl)propanal

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3-(benzimidazol-1-yl)propan-1-ol (100 mg, 0.57 mmol) was dissolved in dichloromethane (6 mL), and treated with sodium periodinane (290 mg, 0.68 mmol). After stirring 5 hours, the mixture was treated with sodium bicarbonate (10 mL), ethyl acetate (10 mL), sodium thiosulfate (2 g) and extracted with ethyl acetate (2×10 mL). The organic phases were combined and washed with brine (15 mL), dried (MgSO4), filtered, and concentrated to yield the desired 3-(benzimidazol-1-yl)propanal (81 mg, 80%) as a yellow oil. 1H NMR (CDCl3) δ 3.09 (t, 2H, J=6 Hz), 4.54 (t, 2H, J=6 Hz), 7.32 (m, 2H), 7.38 (m, 1H), 7.80 (d, 1H, J=6 Hz), 8.00 (s, 1H), 9.81 (s, 1H).

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