Réaction #5222

Équation de réaction

p-toluenesulfonyl chloride

1,8-octanediol

ethyl acetate

sodium azide

→

8-azido-1-octanol

Solvants

methylene chloride

pyridine

dimethylformamide

—

solution

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated gradually overnight for reaction
2. 2
   AutreAfter water washing, the solvent was removed by distillation
3. 3
   Autreto produce an oily residue
4. 4
   Lavagewas washed with water 4 times
5. 5
   Autrethe solvent was removed by distillation
6. 6
   AutreThe object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g

Mode opératoire

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.

Source