반응 #60329

반응 방정식

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

용매

DMF

반응 조건

후처리

1. 1
   온도The reaction was cooled
2. 2
   기타partitioned between EtOAc (200 mL) and H2O (150 mL)
3. 3
   세척The organic phase was washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   건조The solution was dried over MgSO4
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타to provide a residue which
8. 8
   기타was purified by column chromatography (SiO2, 15% EtOAc in hexane)

실험 절차

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.

출처