反応 #60329

反応方程式

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

溶媒

DMF

反応条件

後処理

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

実験手順

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.

出典