반응 #1483030

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

Dess-Martin periodinane

→

4-(tert-butyidiphenylsilyloxy)butanal

용매

—

hexanes

—

hexanes

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타the resulting white precipitant was removed via filtration
2. 2
   농축The solution was concentrated
3. 3
   기타to give
4. 4
   기타form a slurry, which
5. 5
   기타The solids were removed via filtration
6. 6
   농축the resulting solution was concentrated

실험 절차

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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