Ethyl Acetate → HCID 118006058, compound

HRID 926497Notes

Reaction equation

HRID 926497 reaction equation
[N:1]1([C:6]2[CH:21]=[CH:20][C:9]([CH:10]=[C:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.C(OCC)(=O)C>[Pd].C(O)C>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH2:10][CH:11]([C:16](=[O:19])[CH2:17][CH3:18])[C:12]([O:14][CH3:15])=[O:13])=[CH:20][CH:21]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 118006223HCID 118006223, compound

Product 1

HCID 118006058HCID 118006058, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture containing methyl 2-(4-(1H-pyrazol-1-yl)benzylidene)-3-oxopentanoate (mixture of alkene isomers, 3.5 g, 12 mmol, Intermediate 32: step a) and wet 10% palladium on carbon (2.6 g) in ethanol (123 mL) was stirred at 23° C. under an atmosphere of hydrogen gas (balloon pressure). After 2 hours, the reaction mixture was degassed by bubbling nitrogen gas through the solution. The degassed mixture was filtered through Celite®, rinsing with ethanol. The filtrate was concentrated to afford a colorless oil. Ethyl acetate (100 mL) was added. Celite® (8 g) was added to the solution and the solvent was removed by rotary evaporation to afford a free-flowing powder. The powder was loaded onto a column of silica gel for purification. Elution with hexanes initially, grading to 40% ethyl acetate-hexanes provided the title compound as a clear, colorless oil.

Workup

  1. customthe reaction mixture was degassed
  2. customby bubbling nitrogen gas through the solution
  3. filtrationThe degassed mixture was filtered through Celite®
  4. washrinsing with ethanol
  5. concentrationThe filtrate was concentrated
  6. customto afford a colorless oil
  7. additionCelite® (8 g) was added to the solution
  8. customthe solvent was removed by rotary evaporation
  9. customto afford a free-flowing powder
  10. customThe powder was loaded onto a column of silica gel for purification
  11. washElution with hexanes initially

Sources & evidence

ORD record
ord-0ab702af82804a03a91c44976efb7229
Source dataset
uspto-grants-2016_03
Patent number
US09284308B2

Reaction notes

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