Ethyl Acetate → 3-Pyridinol, 6-amino-2-(trifluoromethyl)-

HRID 1049343Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1049343
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([NH2:19])=[N:13][C:14]=2[C:15]([F:18])([F:17])[F:16])O1.B(O[O-])=[O:22].O.[Na+].CCOC(C)=O>C1COCC1.O>[NH2:19][C:12]1[N:13]=[C:14]([C:15]([F:18])([F:17])[F:16])[C:9]([OH:22])=[CH:10][CH:11]=1

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 23695970Perboric acid, sodium salt, monohydrateHCID 904024785-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine

Produkt 1

HCID 904033283-Pyridinol, 6-amino-2-(trifluoromethyl)-Ausbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6-(trifluoromethyl)pyridin-2-amine (0.598 g, 2.076 mmol) in THF (10 mL) and water (10 mL) was treated with sodium perborate monohydrate (0.332 g, 3.32 mmol) and stirred at RT overnight. The mixture was treated with EtOAc and the solids removed via filtration through diatomaceous earth. The filtrate was treated with brine, extracted with EtOAc (3×) and the combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford 6-amino-2-(trifluoromethyl)pyridin-3-ol (92 mg, 25%). 1H NMR (400 MHz, DMSO-d6): δ 9.47 (s, 1H), 7.15 (d, J=8.9 Hz, 1H), 6.58 (d, J=8.9 Hz, 1H), 5.70 (s, 2H); MS (ESI) m/z: 179.1 (M+H+).

Aufarbeitung

  1. customthe solids removed via filtration through diatomaceous earth
  2. additionThe filtrate was treated with brine
  3. extractionextracted with EtOAc (3×)
  4. dry with materialthe combined organics were dried over Na2SO4
  5. concentrationconcentrated to dryness
  6. custompurified via silica gel chromatography (EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-d78c7901059e48ef842d85d76c2c542d
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09382228B2

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