反应 #1244274

反应方程式

2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate

DMF

NaN3

→

22

收率 84.1%

5-Azido-2-phenyl-1,3-dioxane

收率 84.1%

溶剂

water

反应条件

后处理

1. 1
   浓缩The reaction was then concentrated to dryness
2. 2
   workup.DISSOLUTIONThe solid was dissolved in water (700 mL)
3. 3
   萃取extracted into EtOAc (3×500 mL)
4. 4
   洗涤The combined organic layers were washed with water (5×)
5. 5
   浓缩concentrated to dryness
6. 6
   其他to afford an orange solid
7. 7
   其他The material was then recrystallized from hexanes

实验过程

To a 1 L round bottom flask was added 2-phenyl-1,3-dioxan-5-yl 4-methylbenzenesulfonate (40 g, 120 mmol) and DMF (500 mL). NaN3 (31.3 g, 478 mmol) was added as a solution in water (150 mL). The reaction was stirred at 105° C. for 2 days. The reaction was then concentrated to dryness. The solid was dissolved in water (700 mL) and extracted into EtOAc (3×500 mL). The combined organic layers were washed with water (5×) and concentrated to dryness to afford an orange solid. The material was then recrystallized from hexanes to afford 20.7 g (84% yield) of 22 as a pale brown solid. 1H NMR (CDCl3, 400 MHz), δ: 3.67 (2H, pseudo t, J=11.59 Hz), 3.78-3.88 (1H, m), 4.36-4.04 (2H, m), 7.36-7.39 (3H, m), 7.45-7.47 (2H, m). Mass Spec (lo-res): Calc'd for C10H11N3O2: 205.09; found: 178.1 (M+H−N2).

来源