Potassium Carbonate → 5-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridine

HRID 623478Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623478
CC1C=CC(S(O[CH2:12][CH:13]([OH:26])[C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:18][CH:19]=2)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[O:26]1[CH2:12][CH:13]1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:23])([F:24])[F:25])=[N:16][CH:15]=1

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 874265272-Hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate

Produkt 1

HCID 874265125-(Oxiran-2-yl)-2-(2,2,2-trifluoroethoxy)pyridineAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 2-hydroxy-2-(6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl 4-methylbenzenesulfonate (1.66 g, 4.25 mmol, Step-4, single enantiomer) and potassium carbonate (1.76 g, 12.8 mmol) in methanol (43 mL) is stirred at room temperature for 2 hours. White precipitate is filtrated and filtrate is concentrated in vacuo. The residue is poured into water, extracted with ethyl acetate and dried over sodium sulfate and concentrated in vacuo to give 0.89 g (95% yield) of the title compound as colorless oil. This material is used for the next reaction (Step-6) without further purification.

Aufarbeitung

  1. filtrationWhite precipitate is filtrated
  2. concentrationfiltrate is concentrated in vacuo
  3. additionThe residue is poured into water
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-481166b934a54a6fb365ab5304310a0a
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302991B2

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