Methyl iodide → 2-Chloro-5-(methoxymethyl)pyridine

HRID 242244

Reaktionsgleichung

Reaktionsgleichung von HRID 242244
[CH3:1]C([O-])(C)C.[K+].[Cl:7][C:8]1[N:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1.IC>C1COCC1>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][O:15][CH3:1])=[CH:12][N:13]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 177161(6-Chloropyridin-3-yl)methanolHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 190109212-Chloro-5-(methoxymethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.6 g (23.0 mmol) potassium tert-butylate are dissolved in 50 ml THF. 3.0 g (20.9 mmol) (6-chloropyridin-3-yl)methanol are added and the mixture is stirred at RT for 15 min. 4.4 g (31.3 mmol) iodomethane are then added and the mixture is stirred for approx. 30 min until the slightly exothermic reaction has subsided. The solvent is removed, the residue is taken up in methylene chloride and the mixture is washed twice with water. The mixture is dried over magnesium sulfate and concentrated and the residue is purified by column chromatography over silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15).

Aufarbeitung

  1. stirringthe mixture is stirred for approx. 30 min until the slightly exothermic reaction
  2. customThe solvent is removed
  3. washthe mixture is washed twice with water
  4. dry with materialThe mixture is dried over magnesium sulfate
  5. concentrationconcentrated
  6. customthe residue is purified by column chromatography over silica gel (Biotage chromatography, mobile phase: cyclohexane/ethyl acetate 85:15)

Quellen und Nachweise

ORD-Eintrag
ord-9814ec3cdbe941e5b1cf3db5ec028312
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653111B2

Verknüpfte Notizen

Wird geladen…