Sodium Methoxide → 1-(6-Methoxy-3-pyridinyl)-1-propanone

HRID 1678069Notes

Reaction equation

HRID 1678069 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[N:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1>CO>[CH3:1][O:2][C:5]1[N:10]=[CH:9][C:8]([C:11](=[O:14])[CH2:12][CH3:13])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 216982991-(6-Chloropyridin-3-yl)propan-1-one

Product 1

HCID 578305631-(6-Methoxy-3-pyridinyl)-1-propanoneYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (2.8 g, 50 mmol) was added to a solution of 1-(6-chloro-pyridin-3-yl)-propan-1-one (2.8 g, 16.5 mmol) in methanol (70 mL) and the reaction mixture was heated under reflux for eighteen hours. The solution was concentrated to fifty percent, diluted with water (100 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated to give product as a colorless oil (2.1 g, 77 percent yield), which was used without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for eighteen hours
  3. concentrationThe solution was concentrated to fifty percent
  4. additiondiluted with water (100 mL)
  5. extractionextracted with ethyl acetate (2×100 mL)
  6. washThe combined extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-745569c5209447429626f19e87c6d2d6
Source dataset
uspto-grants-2011_08
Patent number
US08008487B2

Reaction notes

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