Reaction #60329

Reaction equation

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

Solvents

DMF

Conditions

Workup

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

Procedure

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