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

HRID 474576Notes

Reaction equation

HRID 474576 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2].C(O)=O>C(OCC)(=O)C.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1)#[N:2]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 5373497Ethyl 4-Cyanocinnamate

Product 1

HCID 11435631Ethyl 3-(4-cyanophenyl)propanoateYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

Pd/C (0.6 g, 10%, 50% water wet) was added to a solution of ethyl (2E)-3-(4-cyanophenyl)-2-propenoate (2.7 g, 13.42 mmol) in ethyl acetate (40 mL) under an argon atmosphere. It was mixed with TEA (3.74 mL, 26.8 mmol) and formic acid (2.57 mL, 67.1 mmol). The reaction mixture was refluxed at 90° C. under argon for 1 h. It was filtered through a Celite pad. The filtrate was then washed with water, 5% NaHCO3 solution and brine, dried over Na2SO4, and concentrated to provide the title compound as a pale yellow oil (2.65 g, 97% yield). LCMS: rt=2.94 min, [M+H+]=204.0

Workup

  1. filtrationIt was filtered through a Celite pad
  2. washThe filtrate was then washed with water, 5% NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b5a9fa8d91214e19bd0e6d2ad5301a0e
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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