Reaktion #77709

Reaktionsgleichung

hexane acetone

methyl 3-benzyloxy-6-methoxypicolinate

LiOH.H2O

methyl iodide

→

3-BENZYLOXY-6-METHOXYPICOLINIC ACID

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Filtrationthe mixture was filtered through Celite®
3. 3
   Sonstigethe solvent evaporated
4. 4
   Sonstigeto give a yellow oil

Vorschrift

To a stirred solution of this compound (10.25 g) in toluene (125 mL), warmed in an oil bath at 60° C., was added silver carbonate (16.6 g), then methyl iodide (8.52 g). The resulting mixture was stirred and heated for 3 hours at 60° C. After cooling, the mixture was filtered through Celite® and the solvent evaporated to give a yellow oil. Silica gel chromatography (4:1 hexane/acetone) gave a nearly colorless oil, whose 1H-NMR and MS data were consistent with methyl 3-benzyloxy-6-methoxypicolinate. Hydrolysis of this ester to the title acid 18 was accomplished with LiOH.H2O as described above for related esters.

Quelle