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

HRID 705821

Reaktionsgleichung

Reaktionsgleichung von HRID 705821
[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]

Komponenten

5

Edukt 2

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

Produkt 1

HCID 53425006Ethyl 3-(2,4,6-trifluorophenyl)propanoateAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

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

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6d7f6fd76ca64d2bbbae274533215244
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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