(4-Chloro-3,5-dimethylpyridin-2-YL)methanol → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

HRID 2304813Notes

Reaction equation

HRID 2304813 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([CH2:9][OH:10])[C:3]=1[CH3:11].[CH3:12][O-:13].[Na+]>CN(C)C=O.CO>[OH:10][CH2:9][C:4]1[C:3]([CH3:11])=[C:2]([O:13][CH3:12])[C:7]([CH3:8])=[CH:6][N:5]=1

Participants

5

Reactant 2

HCID 9795246(4-Chloro-3,5-dimethylpyridin-2-YL)methanolHCID 10942334Sodium Methoxide

Product 1

HCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridineYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask equipped with a stirrer, a condenser and a nitrogen bubbler, 4-Chloro-2-hydroxymethyl-3,5-Lutidine (1 eq.) was dissolved in Dimethylformamide (3-9 volumes) and Methanol (1.5-4.5 volumes). Sodium methoxide (4 eq.) was added and the temperature was raised to (95-100ℑ C.). At the end of the reaction the solvent was distilled under vacuum. Water (2 volumes) was added to the residue and the product was extracted with dichloromethane (2×4 volumes). The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product, 2-hydroxymethyl-4-Methoxy-3,5-lutidine, was obtained in 55% yield.

Workup

  1. customIn a round bottom flask equipped with a stirrer, a condenser
  2. temperaturethe temperature was raised to (95-100ℑ C.)
  3. customAt the end of the reaction the solvent
  4. distillationwas distilled under vacuum
  5. additionWater (2 volumes) was added to the residue
  6. extractionthe product was extracted with dichloromethane (2×4 volumes)
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-04f80af5cb3b4739bcd11125451af9cc
Source dataset
uspto-grants-2002_08
Patent number
US06437139B1

Reaction notes

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