Reacción #1483030

Ecuación de reacción

4-(tert-butyidiphenylsilyloxy)butan-1-ol

Dess-Martin periodinane

→

4-(tert-butyidiphenylsilyloxy)butanal

Disolventes

—

hexanes

—

hexanes

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe resulting white precipitant was removed via filtration
2. 2
   ConcentraciónThe solution was concentrated
3. 3
   Otroto give
4. 4
   Otroform a slurry, which
5. 5
   OtroThe solids were removed via filtration
6. 6
   Concentraciónthe resulting solution was concentrated

Procedimiento

To a solution of the 4-(tert-butyidiphenylsilyloxy)butan-1-ol (0.5 g, 1.5 mmol) in dichloromethane (20 mL) was added Dess-Martin periodinane (775 mg, 1.83 mmol). The mixture was stirred for 1 h. The reaction mixture was poured into hexanes and the resulting white precipitant was removed via filtration. The solution was concentrated to give form a slurry, which was dissolved in dichloromethane (5 mL) and again poured into hexanes resulting in the precipitation of white solid. The solids were removed via filtration and the resulting solution was concentrated. This gave 475 mg (97%) of a clear oil: 1H NMR (CDCl3); δ1.04 (s, 9H), 1.89 (m, 2H), 2.55 (m, 2H), 3.69 (t, 2H, J=6.1 Hz)), 7.38 (m, 6H), 7.63 (d, 4H, J=1.7 Hz), 9.79 (t, 1H, J=1.8 Hz).

Fuente