反应 #60329

反应方程式

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

溶剂

DMF

反应条件

后处理

1. 1
   温度The reaction was cooled
2. 2
   其他partitioned between EtOAc (200 mL) and H2O (150 mL)
3. 3
   洗涤The organic phase was washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   干燥The solution was dried over MgSO4
5. 5
   过滤filtered
6. 6
   浓缩concentrated in vacuo
7. 7
   其他to provide a residue which
8. 8
   其他was purified by column chromatography (SiO2, 15% EtOAc in hexane)

实验过程

4-Chloro-7-cyanochroman (Step C) (8.1 g, 42 mmol) was dissolved in dry DMF (90 mL) and NaN3 (4.0 g, 62 mmol) was added and the reaction was heated to 80° C. under N2. After 5 h TLC (SiO2, toluene) showed that no starting chloride was present. The reaction was cooled and partitioned between EtOAc (200 mL) and H2O (150 mL). The organic phase was washed with H2O (2×100 mL) and brine (100 mL). The solution was dried over MgSO4, filtered and concentrated in vacuo to provide a residue which was purified by column chromatography (SiO2, 15% EtOAc in hexane) to provide the title compound.

来源