Реакция #1483030

Уравнение реакции

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

Dess-Martin periodinane

→

4-(tert-butyidiphenylsilyloxy)butanal

Растворители

—

hexanes

—

hexanes

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеthe resulting white precipitant was removed via filtration
2. 2
   КонцентрированиеThe solution was concentrated
3. 3
   Другоеto give
4. 4
   Другоеform a slurry, which
5. 5
   ДругоеThe solids were removed via filtration
6. 6
   Концентрированиеthe resulting solution was concentrated

Методика

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).

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