Dimethylformamide → 2-Phenyl-1-(pyridin-3-yl)propan-1-one

HRID 1088736Notes

Reaction equation

HRID 1088736 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:16]N(C)C=O.[K].IC>O.CC(O)(C)C>[C:1]1([CH:7]([CH3:16])[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 43289002-Phenyl-1-pyridin-3-yl-ethanoneHCID 5462222Potassium

Product 1

HCID 123658102-Phenyl-1-(pyridin-3-yl)propan-1-oneYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of 70 parts of 2-phenyl-1-(3-pyridinyl)ethanone in 225 parts of N,N-dimethylformamide were added dropwise 46.9 parts of 2-methyl-2-propanol, potassium salt under nitrogen atmosphere. Upon complete addition, stirring was continued for 30 minutes at 0° C. The reaction mixture was allowed to reach room temperature and 70 parts of iodomethane were added. The reaction mixture was allowed to stand at room temperature for 8 hours. The mixture was poured into water and the product was extracted with 1,1'-oxybisethane. The extract was washed with water, dried, filtered and evaporated to dry, yielding 30 parts (40%) of 2-phenyl-1-(3-pyridinyl)-1-propanone as a residue (intermediate 8).

Workup

  1. additionUpon complete addition
  2. stirringstirring
  3. customto reach room temperature
  4. waitto stand at room temperature for 8 hours
  5. extractionthe product was extracted with 1,1'-oxybisethane
  6. washThe extract was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customto dry

Sources & evidence

ORD record
ord-5298e42272a64935b911f1bf50dfb5df
Source dataset
uspto-grants-1990_10
Patent number
US04963573

Reaction notes

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