Reacción #7223

Ecuación de reacción

sodium bicarbonate

sodium thiosulfate

sodium

3-(benzimidazol-1-yl)propan-1-ol

→

3-(benzimidazol-1-yl)propanal

Rendimiento 81.6%

Disolventes

ethyl acetate

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (2×10 mL)
2. 2
   Lavadowashed with brine (15 mL)
3. 3
   Secadodried (MgSO4)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated

Procedimiento

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).

Fuente