Formic Acid → Ethyl 3-(4-cyanophenyl)propanoate

HRID 899113Notes

Reaction equation

HRID 899113 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)[CH3:2].C(N(CC)CC)C.C(O)=O>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 367207Ethyl 3-(4-cyanophenyl)prop-2-enoate

Product 1

HCID 11435631Ethyl 3-(4-cyanophenyl)propanoateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Pd/C (5 g, 10%) was added to a solution of 3-(4-cyanophenyl)acrylic acid ethyl ester (50 g, 0.25 mol; see step (i) above) in dry ethyl acetate (500 mL) under a nitrogen atmosphere, followed by triethylamine (50.3 g, 0.5 mol) and formic acid (57.2 g, 1.24 mol). The mixture was refluxed overnight under a nitrogen atmosphere. After the completion of the reaction (monitored by TLC), the mixture was filtered and the filtrate then washed with water, 5% NaHCO3 solution and brine, before being dried over sodium sulfate. Solvent evaporation under reduced pressure yielded 50 g (99%) of the sub-title compound as a pale yellow oil.

Workup

  1. temperatureThe mixture was refluxed overnight under a nitrogen atmosphere
  2. customAfter the completion of the reaction (monitored by TLC)
  3. filtrationthe mixture was filtered
  4. washthe filtrate then washed with water, 5% NaHCO3 solution and brine
  5. dry with materialbefore being dried over sodium sulfate
  6. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-9343dd81ef0246acb71c54f27befc40d
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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