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

HRID 705819Notes

Reaction equation

HRID 705819 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-cc56c762c7744df992c278dd147b2ecc
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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