5-(1-methyl-1H-pyrazol-4-yl)-3-oxo-1-cyclohexenyl propionate → 5-(1-methyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1,3-dione

HRID 1606864Notes

Reaction equation

HRID 1606864 reaction equation
C([O:5][C:6]1[CH2:11][CH:10]([C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)[CH2:9][C:8](=[O:18])[CH:7]=1)(=O)CC>O1CCCC1>[CH3:17][N:15]1[CH:16]=[C:12]([CH:10]2[CH2:9][C:8](=[O:18])[CH:7]([C:6](=[O:5])[CH2:7][CH3:8])[C:6](=[O:5])[CH2:11]2)[CH:13]=[N:14]1

Participants

3

Reactant 1

HCID 146009705-(1-methyl-1H-pyrazol-4-yl)-3-oxo-1-cyclohexenyl propionate

Product 1

HCID 145764915-(1-methyl-1H-pyrazol-4-yl)-2-propionylcyclohexane-1,3-dioneYield 166.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 30.0 g (121 mmols) of 5-(1-methyl-1H-pyrazol-4-yl)-3-oxo-1-cyclohexenyl propionate and 7.4 g (61 mmols) of 4-N,N-dimethylaminopyridine was dissolved in 300 ml of tetrahydrofuran. The solution was heated to reflux for 5 hours to perform the reaction. After completion of the reaction, the reaction mixture was allowed to cool. The reaction solution was concentrated and the product was extracted with chloroform. Water was added to the extract and the aqueous phase was adjusted to pH of 4 to 5. The 4-N,N-dimethylaminopyridine was removed. After washing the chloroform phase with water and drying, the solvent was distilled off under reduced pressure to give 25.0 g of the product.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 hours
  3. customthe reaction
  4. customAfter completion of the reaction
  5. temperatureto cool
  6. concentrationThe reaction solution was concentrated
  7. extractionthe product was extracted with chloroform
  8. additionWater was added to the
  9. extractionextract
  10. customThe 4-N,N-dimethylaminopyridine was removed
  11. washAfter washing the chloroform phase with water
  12. customdrying
  13. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-cbb165e734624980a26cce1fbb009a30
Source dataset
uspto-grants-1989_09
Patent number
US04863504

Reaction notes

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