Reaktion #60329

Reaktionsgleichung

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was cooled
2. 2
   Sonstigepartitioned between EtOAc (200 mL) and H2O (150 mL)
3. 3
   WaschenThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   TrocknenThe solution was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto provide a residue which
8. 8
   Sonstigewas purified by column chromatography (SiO2, 15% EtOAc in hexane)

Vorschrift

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.

Quelle