4-Toluenesulfonyl chloride → Diethyl 5-p-toluenesulfonyloxypentylphosphonate

HRID 2010

Reaction equation

HRID 2010 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1>N1C=CC=CC=1>[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][P:7](=[O:14])([O:8][CH2:9][CH3:10])[O:11][CH2:12][CH3:13])(=[O:23])=[O:22])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 10680635Diethyl 5-hydroxypentylphosphonate

Product 1

HCID 19689184Diethyl 5-p-toluenesulfonyloxypentylphosphonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

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.

Workup

  1. additiontreated
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. washwashed several times with 20% strength citric acid solution and water
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporating the solvent
  6. customwhich was employed without further purification

Sources & evidence

ORD record
ord-6aa4458a36274254b109c6155ed0e1f1
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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