Pyridine → HCID 18987747, compound

HRID 1463272Notes

Reaction equation

HRID 1463272 reaction equation
O[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[CH3:11][C:12]([CH:14]([O:17][CH3:18])[O:15][CH3:16])=[O:13].N1C=CC=CC=1>C1(C)C=CC=CC=1>[CH3:16][O:15][CH:14]([O:17][CH3:18])[C:12]1([CH3:11])[CH2:2][C:3](=[O:4])[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=2[O:13]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 68490alpha-HydroxyacetophenoneHCID 80650Pyruvic aldehyde dimethyl acetal

Product 1

HCID 18987747HCID 18987747, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 250 ml of toluene were dissolved 30 g (0.22 mmole) of 2-hydroxy acetophenone and 33.8(0.29 mmole) of pyruvic aldehyde dimethyl acetal; and, 6.3 ml (0.09 mmole) of pyridine was added thereto. After stirring at room temperature 30 minutes, the reactants were heated to reflux for 5 hours using Dean-Stark apparatus. The solvent was removed under reduced pressure and 100 ml of 2N HCl aqueous solution was added. The resultant solution was stirred for 1 hour at room temperature, extracted with ethyl acetate (20 ml×2), washed with 100 ml of water and then with 50 ml of saturated sodium chloride aqueous solution and purified by silica gel column chromatography using a mixture of hexane and ethyl acetate (4:1) to obtain 39 g (0.16 mmole, yield 75%) of the title compound as a white solid.

Workup

  1. temperaturethe reactants were heated
  2. temperatureto reflux for 5 hours
  3. customThe solvent was removed under reduced pressure and 100 ml of 2N HCl aqueous solution
  4. additionwas added
  5. stirringThe resultant solution was stirred for 1 hour at room temperature
  6. extractionextracted with ethyl acetate (20 ml×2)
  7. washwashed with 100 ml of water
  8. customwith 50 ml of saturated sodium chloride aqueous solution and purified by silica gel column chromatography
  9. additiona mixture of hexane and ethyl acetate (4:1)

Sources & evidence

ORD record
ord-cce73e3f82f841f5b75e177f8b2e7af1
Source dataset
uspto-grants-1994_04
Patent number
US05300511

Reaction notes

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