Trifluoroacetic acid → 2-(6-(Trifluoromethyl)pyridin-2-yl)acetic acid

HRID 1910066Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1910066
CC([CH:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]=1)[C:6]([O-:8])=[O:7])(C)C.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>ClCCl>[F:17][C:15]([F:16])([F:18])[C:11]1[N:10]=[C:9]([CH2:5][C:6]([OH:8])=[O:7])[CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 867621751,1-Dimethylethyl[6-(trifluoromethyl)-2-pyridinyl]acetate

Produkt 1

HCID 534015132-(6-(Trifluoromethyl)pyridin-2-yl)acetic acidAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl[6-(trifluoromethyl)-2-pyridinyl]acetate (698 mg, 2.67 mmol), triethylsilane (1.067 mL, 6.68 mmol) in Dichloromethane (DCM) (10 mL) was added TFA (2.68 mL, 34.7 mmol) dropwise via syringe. The reaction was stirred overnight at room temperature. LCMS analysis indicated good conversion, so the reaction was concentrated to a yellow oil. 5 mL of diethyl ether was added but no precipitation occurred, so the solution was concentrated to afford [6-(trifluoromethyl)-2-pyridinyl]acetic acid (535 mg, 2.61 mmol, 98% yield) as a yellow oil which solidified to a yellow solid. LC-MS (ES) m/z=206 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.89 (s, 2H), 7.70 (d, J=7.83 Hz, 1H), 7.81 (d, J=7.58 Hz, 1H), 7.97-8.16 (m, 1H), 12.26-12.88 (br. s., 1H).

Aufarbeitung

  1. concentrationso the reaction was concentrated to a yellow oil
  2. addition5 mL of diethyl ether was added
  3. customno precipitation
  4. concentrationwas concentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7c2bf9b42e04b6d811949178044671f
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598156B2

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