反応 #1483030

反応方程式

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

Dess-Martin periodinane

→

4-(tert-butyidiphenylsilyloxy)butanal

溶媒

—

hexanes

—

hexanes

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   その他the resulting white precipitant was removed via filtration
2. 2
   濃縮The solution was concentrated
3. 3
   その他to give
4. 4
   その他form a slurry, which
5. 5
   その他The solids were removed via filtration
6. 6
   濃縮the resulting solution was concentrated

実験手順

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).

出典