Reaction #2106

Reaction equation

diethyl 5-hydroxypentylphosphonate

4-toluenesulfonyl chloride

→

Diethyl 5-p-toluenesulfonyloxypentylphosphonate

Solvents

pyridine

Conditions

Workup

1. 1
   workup.ADDITIONtreated
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   Washwashed several times with 20% strength citric acid solution and water
4. 4
   Dryingdried over sodium sulfate
5. 5
   OtherAfter evaporating the solvent
6. 6
   Otherwhich was employed without further purification

Procedure

30 g (0.134 mol) of diethyl 5-hydroxypentylphosphonate (see Example 21) were dissolved in 200 ml of pyridine, and the solution was cooled to 0° C. and treated with stirring with 26.1 g (0.134 mol) of 4-toluenesulfonyl chloride. The reaction mixture was concentrated under reduced pressure, taken up in ethyl acetate, washed several times with 20% strength citric acid solution and water and dried over sodium sulfate. After evaporating the solvent, a pale yellow oil remained, which was employed without further purification.

Source