Sodium Bicarbonate → Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-

HRID 623421

Reaktionsgleichung

Reaktionsgleichung von HRID 623421
CON(C)[C:4](=[O:17])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[N:7][CH:6]=1.[CH3:19][Mg]Br.C(=O)([O-])O.[Na+]>O1CCCC1>[F:16][C:13]([F:14])([F:15])[CH2:12][O:11][C:8]1[N:7]=[CH:6][C:5]([C:4](=[O:17])[CH3:19])=[CH:10][CH:9]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 86707284N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)pyridine-3-carboxamideHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 58629124Ethanone, 1-[6-(2,2,2-trifluoroethoxy)-3-pyridinyl]-Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of N-methoxy-N-methyl-6-(2,2,2-trifluoroethoxy)nicotinamide (6.54 g, 24.8 mmol, Step-2) in tetrahydrofuran (80 mL) is added dropwise 1.06M methylmagnesium bromide (46.7 mL, 49.5 mmol) at 0° C. The reaction mixture is stirred at room temperature for 1.5 hours. The reaction mixture is poured into saturated aqueous sodium hydrogen carbonate (100 mL) and extracted with ethyl acetate (300 mL). The organic layer is washed with water (100 mL×2) and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1) to give 4.51 g (83% yield) of the title compound as colorless oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate (300 mL)
  2. washThe organic layer is washed with water (100 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-022f4767b1264c60b3aa5b35c2f153ea
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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