Dimethyl Sulfoxide → 4-Methoxy-2,3,5-trimethylpyridine

HRID 2231951Notes

Reaction equation

HRID 2231951 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]=1[CH3:10].[CH3:11][O-:12].[Na+].CS(C)=O>O>[CH3:11][O:12][C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH3:9])[C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 10942334Sodium MethoxideHCID 142036064-Chloro-2,3,5-trimethylpyridine

Product 1

HCID 1278994-Methoxy-2,3,5-trimethylpyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60 g (0.39 mol) 4-chloro-2,3,5-trimethylpyridine and 21.7 g (0.40 mol) sodium methoxide and 180 ml dry dimethylsulfoxide was heated with stirring to 55°-60° C. for 8 hrs. The reaction mixture was diluted with 600 ml water and extracted with 3x100 ml toluene and the organic layer washed with 2x50 ml water. The organic phase was added to 200 ml water and pH adjusted to 4.1 with stirring. This process was repeated twice with 200 ml and 100 ml of water. The organic layer contained almost pure starting material. The combined water phase was made alkaline and extracted with 2×150 ml methylene chloride. Evaporation of solvent gave 40.7 g of almost pure 4-methoxy-2,3,5-trimethylpyridine. NMR: 2×3H, 2,2: 3H, 2,45(s); 3H, 3,75(s); 1H, 8,2(s). (CDCl3)

Workup

  1. extractionextracted with 3x100 ml toluene
  2. washthe organic layer washed with 2x50 ml water
  3. additionThe organic phase was added to 200 ml water
  4. stirringwith stirring
  5. extractionextracted with 2×150 ml methylene chloride
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-ad85c31c4b194a389dfb49be6a7d6a76
Source dataset
uspto-grants-1988_11
Patent number
US04785113

Reaction notes

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