Reacción #5222

Ecuación de reacción

p-toluenesulfonyl chloride

1,8-octanediol

ethyl acetate

sodium azide

→

8-azido-1-octanol

Disolventes

methylene chloride

pyridine

dimethylformamide

—

solution

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated gradually overnight for reaction
2. 2
   OtroAfter water washing, the solvent was removed by distillation
3. 3
   Otroto produce an oily residue
4. 4
   Lavadowas washed with water 4 times
5. 5
   Otrothe solvent was removed by distillation
6. 6
   OtroThe object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g

Procedimiento

14.65 g of 1,8-octanediol was dissolved in 80 g of pyridine, and cooled to 10° C. A solution of 19 g p-toluenesulfonyl chloride in 70 ml anhydrous methylene chloride was added dropwise thereto, and the mixture was heated gradually overnight for reaction. After water washing, the solvent was removed by distillation, to produce an oily residue. The residue was dissolved in dimethylformamide to a 200 ml solution, to which was added 20 g of sodium azide, and the resultant mixture was maintained at 80° C. for 2 hours for reaction. The mixture was, after added with ethyl acetate, was washed with water 4 times and the solvent was removed by distillation. The object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g.

Fuente