Formic Acid → Ethyl 3-(2,4,6-trifluorophenyl)propanoate

HRID 705821Notes

Reaction equation

HRID 705821 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

HCID 284Formic AcidHCID 574127793-(2,4,6-Trifluoro-phenyl)-acrylic acid ethyl ester

Product 1

HCID 53425006Ethyl 3-(2,4,6-trifluorophenyl)propanoateYield 89.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

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

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe filtrate was then washed with water, 5% NaHCO3 solution and brine
  3. dry with materialbefore being dried over Na2SO4
  4. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-6d7f6fd76ca64d2bbbae274533215244
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…