Reaktion #157687

ord-aa61374f8ec849648462943e19247edb

Reaktionsgleichung

CI
methyl iodide
CCOC(=O)c1ccc(C2CC2)c(O)n1
ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate
CCOC(=O)c1ccc(C2CC2)c(OC)n1
ethyl 5-cyclopropyl-6-methoxypyridine-2-carboxylate
Ausbeute 99.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
60°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationThe reaction solution was filtered through celite
  2. 2
    Sonstigethe solvent was evaporated under reduced pressure
  3. 3
    SonstigeThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1)

Vorschrift

Silver carbonate (70 g) and methyl iodide (11.2 mL) were added to a solution of ethyl 5-cyclopropyl-6-hydroxypyridine-2-carboxylate (12.4 g) in chloroform (250 mL), and the mixture was stirred at 60° C. for eight hours. The reaction solution was filtered through celite, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→4:1) to give ethyl 5-cyclopropyl-6-methoxypyridine-2-carboxylate (13.05 g, 99%) as a colorless oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08822503B2uspto-grants-2014_09