Diethyl Ether → 1-(4-Methoxy-pyridin-2-yl)-ethanone

HRID 379770Notes

Reaction equation

HRID 379770 reaction equation
CO[C:3]1[CH:8]=[CH:7][N:6]=[C:5](C#N)[CH:4]=1.C[Mg]I.C(=O)(O)[O-:15].[Na+].C[CH2:20][O:21][CH2:22][CH3:23]>C1C=CC=CC=1>[C:4]([C:5]1[CH:23]=[C:22]([O:21][CH3:20])[CH:8]=[CH:7][N:6]=1)(=[O:15])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl Ether2×HCID 516892Sodium BicarbonateHCID 134151564-Methoxypyridine-2-carbonitrileHCID 178418373HCID 178418373, compound

Product 1

HCID 218168161-(4-Methoxy-pyridin-2-yl)-ethanoneYield 60%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 4-methoxy-2-pyridinecarbonitrile (5.35 g, 38.6 mmol) in benzene (50 ml) and ether (50 ml) cooled to 0° C. was added dropwise over 20 min a 2M slution of MeMgI in ether (23 ml, 46.3 mmol). After 0.5 h, the mixture was allowed to warm to ambient temperature, and stirring continued for 2 h. The mixture was cooled to 0° C. and 2M aqueous HCI (100 ml) added. The mixture was made basic with saturated aqueous sodium bicarbonate (˜80 ml) and the organic layer separated and dried (MgSO4). After removal of solvent, the residue was purified by flash chromatography eluting with ethyl acetate/hexane (1:5) to afford 3.60 g (60%) of 2-acetyl-4-methoxypyridine.

Workup

  1. waitcontinued for 2 h
  2. temperatureThe mixture was cooled to 0° C.
  3. addition2M aqueous HCI (100 ml) added
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. customAfter removal of solvent
  7. customthe residue was purified by flash chromatography
  8. washeluting with ethyl acetate/hexane (1:5)

Sources & evidence

ORD record
ord-dc6c312a93024699b2e695fe61858af0
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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