Dimethyl Sulfoxide → 3-(Benzyloxy)-2-chloropyridine

HRID 1904006Notes

Reaction equation

HRID 1904006 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[O-]CC.[Na+].CS(C)=O.[CH2:17](Cl)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[Cl:1][C:2]1[C:7]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 7503Benzyl Chloride2×HCID 811362-Chloro-3-pyridinolHCID 2723922Sodium ethoxide

Product 1

HCID 8193743-(Benzyloxy)-2-chloropyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Chloro-3-hydroxypyridine (9.47 g; 0.073 moles) was added to a solution of sodium ethoxide in ethanol (from sodium, 1.67 g; 0.073 g. atom). Sufficient dimethyl sulphoxide was added to dissolve all of the solid, and ethanol was removed in vacuo. To the resulting solution was added benzyl chloride (9.3 g; 0.073 moles) with cooling and stirring, and the reaction mixture was left to stir under reflux for 6 hours. Unreacted benzyl chloride, and solvent, were evaporated off under vacuum on a boiling water bath, and the residue was treated with water to precipitate out an oil which was extracted with chloroform, washed with N sodium hydroxide solution and dried over anhydrous magnesium sulfate. After removing the solvent, 2-chloro-3-benzyloxypyridine was obtained as a solid (11.63 g, mp 36°-8°).

Workup

  1. customwas removed in vacuo
  2. temperaturewith cooling
  3. waitthe reaction mixture was left
  4. stirringto stir
  5. temperatureunder reflux for 6 hours
  6. customwere evaporated off under vacuum on a boiling water bath
  7. additionthe residue was treated with water
  8. customto precipitate out an oil which
  9. extractionwas extracted with chloroform
  10. washwashed with N sodium hydroxide solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customAfter removing the solvent

Sources & evidence

ORD record
ord-c61ef1a27b6c410a9b9953f12e402f3f
Source dataset
uspto-grants-1984_03
Patent number
US04439437

Reaction notes

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