Reacción #7191

Ecuación de reacción

3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propan-1-ol

Dess-Martin reagent

→

title compound

Rendimiento 76.7%

3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propionaldehyde

Rendimiento 76.7%

Disolventes

ethyl acetate

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 1N NaOH, brine
2. 2
   Secadodried over Na2SO4
3. 3
   OtroEvaporation of the solvent and flash chromatograph of residue over silica gel

Procedimiento

To a solution of 3-(1-tert-butoxycarbonyl-Benzimidazol-2-yl)propan-1-ol (186 mg, 0.67 mmol) in CH2Cl2 (4 mL) was added Dess-Martin reagent (314 mg, 0.74 mmol) and the resulting mixture was allowed to stir at room temperature under N2 for 1 hour. The mixture was further diluted with 300-mL ethyl acetate, and washed with 1N NaOH, brine and dried over Na2SO4. Evaporation of the solvent and flash chromatograph of residue over silica gel, using 20% ethyl acetate in CH2Cl2, gave the title compound (141 mg, 76%) as pure white solid. 1H NMR (CDCl3) □ 1.72 (s, 9H), 3.13 (t, 2H, J=6.8 Hz), 3.52 (t, 2H, J=6.8 Hz), 7.28–7.34 (m, 2H), 7.66–7.67 (m, 1H), 7.87–7.91 (m, 1H), 9.97 (s, 1H).

Fuente