Ethyl Acetate → 1-(2,6-Difluoropyridin-3-yl)ethanone

HRID 1436098Notes

Reaction equation

HRID 1436098 reaction equation
C[Mg]Br.[F:4][C:5]1[N:16]=[C:15]([F:17])[CH:14]=[CH:13][C:6]=1[C:7](N(OC)C)=[O:8].[Cl-].[NH4+].[C:20](OCC)(=O)C>C1COCC1>[F:4][C:5]1[C:6]([C:7](=[O:8])[CH3:20])=[CH:13][CH:14]=[C:15]([F:17])[N:16]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 866126072,6-difluoro-N-methoxy-N-methylnicotinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 251322441-(2,6-Difluoropyridin-3-yl)ethanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methylmagnesium bromide in THF (0.96 M, 88.1 mL) was added to a solution of 2,6-difluoro-N-methoxy-N-methylnicotinamide (7.01 g) in tetrahydrofuran (180 mL) under ice-cooling, and the reaction solution was stirred under ice-cooling for two hours. A saturated ammonium chloride solution and ethyl acetate were added to the reaction solution under ice-cooling, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate) to obtain 4.74 g of the title compound.

Workup

  1. temperaturecooling
  2. temperaturecooling for two hours
  3. temperaturecooling
  4. customthe organic layer was separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel column chromatography (elution solvent: hexane-ethyl acetate)

Sources & evidence

ORD record
ord-1e1db8592c654b9b8f23c3ffc463446e
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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