تفاعل #60329

معادلة التفاعل

NaN3

4-Chloro-7-cyanochroman

toluene

chloride

→

title compound

4-azido-7-cyanochroman

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe reaction was cooled
2. 2
   أخرىpartitioned between EtOAc (200 mL) and H2O (150 mL)
3. 3
   غسيلThe organic phase was washed with H2O (2×100 mL) and brine (100 mL)
4. 4
   تجفيفThe solution was dried over MgSO4
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated in vacuo
7. 7
   أخرىto provide a residue which
8. 8
   أخرىwas purified by column chromatography (SiO2, 15% EtOAc in hexane)

الإجراء التجريبي

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.

المصدر