ethyl (E)-4,4-dimethyl-5-phenyl-2-pentenoate → Ethyl 4,4-dimethyl-5-phenylpentanoate

HRID 1610656Notes

Reaction equation

HRID 1610656 reaction equation
[CH3:1][C:2]([CH3:17])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]>C(O)C.[Pd]>[CH3:17][C:2]([CH3:1])([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

4

Reactant 1

HCID 57446329ethyl (E)-4,4-dimethyl-5-phenyl-2-pentenoate

Product 1

HCID 10879068Ethyl 4,4-dimethyl-5-phenylpentanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl (E)-4,4-dimethyl-5-phenyl-2-pentenoate (55.97 g, 240.9 mmol) in ethanol (150 ml) was hydrogenated using 10% palladium/carbon (containing water by 50%) (5 g) as a catalyst at room temperature overnight under normal pressure. The recovered catalyst of the reaction solution was filtered off and the catalyst was washed with ethanol. The recovered solvent of the filtrate was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1) to give the objective substance.

Workup

  1. customat room temperature
  2. customovernight
  3. filtrationThe recovered catalyst of the reaction solution was filtered off
  4. washthe catalyst was washed with ethanol
  5. customThe recovered solvent of the filtrate was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (hexane/ethyl acetate=15/1-9/1)
  8. customto give the objective substance

Sources & evidence

ORD record
ord-1fe355f061bd4287badc5e6c22ad3d1c
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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