Benzophenone → HCID 66668715, compound

HRID 1617619Notes

Reaction equation

HRID 1617619 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].[C:12]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C)C(=O)C>[OH:19][C:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:2][C:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 142824-AcetylpyridineHCID 24758Sodium hydride

Product 1

HCID 66668715HCID 66668715, compoundYield 3.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 4-acetylpyridine (1.25 g) in N,N-dimethylacetamide (10 ml) was added NaH (0.413 g, as a 55% suspension in mineral oil) at 0° C. After stirring for 30 min, benzophenone (1.882 g) was added. After 30 min, the cooling bath was removed. The mixture was stirred overnight at room temperature. The mixture was cooled to 0° C. NaH (0.413 g, as a 55% suspension in mineral oil) was added and the mixture was stirred for 3 h. Water and ethyl acetate were added. The pH was adjusted to 8 using 1 M aqueous HCl. The mixture was extracted with ethyl acetate. The organic phase was dried using MgSO4, filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1) to give the title compound (119 mg) as a colorless solid, MS (ESI+): m/z=304.2 [M+H]+.

Workup

  1. customat 0° C
  2. waitAfter 30 min
  3. customthe cooling bath was removed
  4. stirringThe mixture was stirred overnight at room temperature
  5. additionNaH (0.413 g, as a 55% suspension in mineral oil) was added
  6. stirringthe mixture was stirred for 3 h
  7. additionWater and ethyl acetate were added
  8. extractionThe mixture was extracted with ethyl acetate
  9. customThe organic phase was dried
  10. filtrationfiltered
  11. concentrationconcentrated to dryness
  12. customThe product was purified by chromatography (SiO2, cyclohexane/ethyl acetate 1:0 to 0:1)

Sources & evidence

ORD record
ord-408ba13fa8da4a0692264223348e4778
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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