Water → 4-Methoxy-2,6-dimethylpyridine

HRID 2304815Notes

Reaction equation

HRID 2304815 reaction equation
C[O-].[Na+].CN(C)[CH:6]=[O:7].Cl[C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([CH3:17])[CH:11]=1.O>CO>[CH3:6][O:7][C:10]1[CH:15]=[C:14]([CH3:16])[N:13]=[C:12]([CH3:17])[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 5881754-Chloro-2,6-dimethylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 157642254-Methoxy-2,6-dimethylpyridineYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2 eq.) was dissolved in methanol (1.5 volumes) and dry dimethylformamide (2 volumes). The solution was heated to (95-100ℑ C.)and while stirring under a stream of nitrogen, 4-chlorolutidine (1 eq.) was added dropwise. At the end of the reaction (about 2 hours), the mixture was cooled in an ice bath and cold water (10 volumes) was added. The product was extracted with dichloromethane (3×2 volumes). The combined organic extracts were dried over sodium sulfate, filtered and the solvent was evaporated under vacuum. Light yellow oil was obtained in 72% yield.

Workup

  1. temperatureThe solution was heated to (95-100ℑ C.)and
  2. additionwas added dropwise
  3. customAt the end of the reaction (about 2 hours)
  4. temperaturethe mixture was cooled in an ice bath
  5. extractionThe product was extracted with dichloromethane (3×2 volumes)
  6. dry with materialThe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under vacuum
  9. customLight yellow oil was obtained in 72% yield

Sources & evidence

ORD record
ord-93a4ba6779624930b77acb1d50a79f18
Source dataset
uspto-grants-2002_08
Patent number
US06437139B1

Reaction notes

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