Ammonium formate → Ethyl 5-methyl-5-phenylpentanoate

HRID 840968Notes

Reaction equation

HRID 840968 reaction equation
[CH3:1][C:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7].C([O-])=O.[NH4+]>[C].[Pd].C(O)C>[CH3:1][CH:2]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 70170845Ethyl 5-methyl-5-phenyl-4-pentenoate

Product 1

HCID 22620530Ethyl 5-methyl-5-phenylpentanoateYield 95%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
72.5 °C

Procedure

A mixture of ethyl 5-methyl-5-phenyl-4-pentenoate (17.0 g, 77.9 mmol), ammonium formate (49.1 g, 779 mmol), 10% palladium-carbon (1.7 g) and ethanol (350 ml) was stirred at 70-75° C. for 1 hour. The catalyst was filtered off and the filtrate obtained was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with a 5% aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure, and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98) to obtain 16.3 g of ethyl 5-methyl-5-phenylpentanoate.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate obtained
  3. concentrationwas concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with a 5% aqueous sodium chloride solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/98)

Sources & evidence

ORD record
ord-332b858232ee49f2bcede9f8ae54b721
Source dataset
uspto-grants-2002_04
Patent number
US06369110B1

Reaction notes

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