Réaction #60329

Équation de réaction

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was cooled
2. 2
   Autrepartitioned between EtOAc (200 mL) and H2O (150 mL)
3. 3
   LavageThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   SéchageThe solution was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autreto provide a residue which
8. 8
   Autrewas purified by column chromatography (SiO2, 15% EtOAc in hexane)

Mode opératoire

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.

Source