Ethyl Acetate → 1-(4-pyridin-2-yl-phenyl)-ethanone

HRID 1871644Notes

Reaction equation

HRID 1871644 reaction equation
C[Mg]Br.C([O:6][CH2:7][CH3:8])C.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:22]=[CH:21][C:18](C#N)=[CH:17][CH:16]=1.[Cl-].[NH4+].C(OCC)(=O)C>ClCCl>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:16]=[CH:17][C:18]([C:7](=[O:6])[CH3:8])=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 15152384-(2-Pyridyl)benzonitrileHCID 178467822HCID 178467822, compound

Product 1

HCID 109654721-(4-pyridin-2-yl-phenyl)-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After 21 ml of a 3M methyl magnesium bromide-diethyl ether solution was added dropwise to a solution of 3.10 g of 4-(2-pyridyl)benzonitrile in 120 ml of dichloromethane under ice-cooling in a nitrogen atmosphere, the mixture was stirred at room temperature for 20 hours. After the reaction, an aqueous ammonium chloride solution and ethyl acetate were added to the reaction mixture, followed by stirring of the resulting mixture. The ethyl acetate layer was separated from the reaction mixture, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:2) to obtain the crude desired compound as crystals. Further, the crude compound was washed with diisopropyl ether-hexane to obtain 1.56 g of the desired compound.

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. customAfter the reaction
  3. stirringby stirring of the resulting mixture
  4. customThe ethyl acetate layer was separated from the reaction mixture
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain the crude desired compound as crystals
  8. washFurther, the crude compound was washed with diisopropyl ether-hexane

Sources & evidence

ORD record
ord-6e4520d77c11416c805248261a060693
Source dataset
uspto-grants-2000_08
Patent number
US06103907

Reaction notes

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