Formic Acid → Ethyl 3-(2,4,6-trifluorophenyl)propanoate
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(O)=O>C(OCC)(=O)C.[Pd]>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([F:9])[C:3]=1[CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
Pd/C (0.5 g, 10%, 50% water wet) was added to a solution of ethyl (2E)-3-(2,4,6-trifluorophenyl)-2-propenoate (2.0 g, 8.69 mmol) in ethyl acetate (40 mL) under an argon atmosphere, followed by TEA (2.409 mL, 17.38 mmol) and formic acid (1.666 mL, 43.4 mmol). The reaction mixture was refluxed at 90° C. under argon for 1 h. The reaction mixture was filtered through a celite pad and the filtrate was then washed with water, 5% NaHCO3 solution and brine, before being dried over Na2SO4. Solvent evaporation under reduced pressure yielded the title compound as a pale yellow oil (1.8 g, 89% yield). LCMS: 3.41 min, [M+H+]=232.9
Workup
- filtrationThe reaction mixture was filtered through a celite pad
- washthe filtrate was then washed with water, 5% NaHCO3 solution and brine
- dry with materialbefore being dried over Na2SO4
- customSolvent evaporation under reduced pressure
Sources & evidence
- ORD record
- ord-2561cc9229fa448e9f3488b49383699c
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637536B2
Reaction notes
Loading…