4-Toluenesulfonyl chloride → 4-(3-Chloropropyl)pyridine

HRID 1615079Notes

Reaction equation

HRID 1615079 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9]O)=[CH:3][CH:2]=1.CC1C=CC(S([Cl:21])(=O)=O)=CC=1>N1C=CC=CC=1>[Cl:21][CH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 729234-Pyridinepropanol

Product 1

HCID 2054424-(3-Chloropropyl)pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-pyridin-4-yl-propan-1-ol (3.1 g) in pyridine (8 mL) was added 4-methylbenzenesulfonyl chloride (5.0 g) at 0° C. The reaction mixture was stirred at RT for 12 hr. The reaction mixture was concentrated in vacuo. Saturated aqueous NaHCO3 was added to the residue and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over Na2SO4. The solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/2) to give the title compound (2.1 g, 61%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionSaturated aqueous NaHCO3 was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was purified by silica gel chromatography (Developing solvent: hexane/ethyl acetate=1/2)

Sources & evidence

ORD record
ord-ef843ce7f4f54e8883f9c715ad67502c
Source dataset
uspto-grants-2014_07
Patent number
US08765739B2

Reaction notes

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