Potassium Carbonate → HCID 11241368, compound

HRID 856587Notes

Reaction equation

HRID 856587 reaction equation
C([CH:3]([C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1)#N.C(=O)([O-])[O-:19].[K+].[K+]>O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)=[O:19])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11183726HCID 11183726, compound

Product 1

HCID 11241368HCID 11241368, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(α-cyano-4-fluorobenzyl)-4-methylpyridine (3.1 g) and potassium carbonate (2.9 g) were suspended in 20% hydrated dimethylsulfoxide (150 ml), and the suspension was stirred overnight. The mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then, the solvent was distilled off. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane), to give 2-(4-fluorobenzoyl)-4-methylpyridine (1.6 g) as brown crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-11ac5fb20da64060929094e6d82c09f0
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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