Reaction #5222

Reaction equation

p-toluenesulfonyl chloride

1,8-octanediol

ethyl acetate

sodium azide

→

8-azido-1-octanol

Solvents

methylene chloride

pyridine

dimethylformamide

—

solution

Conditions

Workup

1. 1
   Temperaturethe mixture was heated gradually overnight for reaction
2. 2
   OtherAfter water washing, the solvent was removed by distillation
3. 3
   Otherto produce an oily residue
4. 4
   Washwas washed with water 4 times
5. 5
   Otherthe solvent was removed by distillation
6. 6
   OtherThe object compound was isolated by silica-gel column-chromatography (CHCl3 -AcOEt 5:1-1:1) The yield was 6.07 g

Procedure

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