4-Toluenesulfonyl chloride → 2-(Chloromethyl)-4-methylpyridine

HRID 1419853Notes

Reaction equation

HRID 1419853 reaction equation
[N+:1]1([O-])[C:2]([CH3:8])=[CH:3][C:4]([CH3:7])=[CH:5][CH:6]=1.C1(C)C=CC(S([Cl:19])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:19][CH2:8][C:2]1[CH:3]=[C:4]([CH3:7])[CH:5]=[CH:6][N:1]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 707332,4-Dimethylpyridine 1-oxide

Product 1

HCID 126752612-(Chloromethyl)-4-methylpyridineYield 364.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2,4-Lutidine-1-oxide (10 g, 8.10 mmol) was dissolved in anhydrous dioxane (125 ml) under nitrogen atomsphere, and herein p-toluenesulfonyl chloride (31.5 g, 162 mmol) was added and refluxed for 5 hours. The solution was neutralized with the saturated aqueous solution of potassium carbonate and extracted twice with methylene chloride. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to get crude product. The residue was separated and purified by column-chromatography over silica gel to obtain 2-chloromethyl-4-methylpyridine (4.18 g, yield=36%).

Workup

  1. temperaturerefluxed for 5 hours
  2. extractionextracted twice with methylene chloride
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto get crude product
  7. customThe residue was separated
  8. custompurified by column-chromatography over silica gel

Sources & evidence

ORD record
ord-89510358d4574b16ad92508c4a546108
Source dataset
uspto-grants-1999_03
Patent number
US05889027

Reaction notes

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