Water → HCID 58520617, Verbindung

HRID 511819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511819
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1.O>CN(C=O)C>[CH:17]1([CH2:16][O:8][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[N:7][CH:6]=2)[CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 142752-Methyl-5-hydroxypyridineHCID 81503Bromomethylcyclopropane

Produkt 1

HCID 58520617HCID 58520617, VerbindungAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-methylpyridin-3-ol (5.0 g, 46 mmol) in DMF (45 mL) were added cesium carbonate (16.5 g, 53 mmol) and (bromomethyl)cyclopropane (7.1 g, 53 mmol) at room temperature. After being stirred at room temperature for 18 hours, the mixture was poured into H2O, and the aqueous phase was extracted with ethyl acetate (twice). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1 (v/v)) to give 3.9 g (52% yield) of the title compound as a yellow oil:

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate (twice)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (3:1 (v/v))

Quellen und Nachweise

ORD-Eintrag
ord-643c4c32de0c4749881b1d0b8f1a1bc6
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09101616B2

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