Reaktion #306266

Reaktionsgleichung

(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol

methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate

THF

lithium tetrahydroaluminate

THF

→

title compound

7-Methoxy-4-((5-phenyl-[1,2,3]-triazolo[1,5-a]pyridin-3-yl)methoxy)quinoline

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturTo a cooled
2. 2
   Waschenwashed with water, sat. NaHCO3
3. 3
   Trocknenthe organic layer dried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   workup.ADDITIONwere added
6. 6
   WaschenThe organic layer was washed with sat NaHCO3
7. 7
   Trocknendried over Na2SO4
8. 8
   Filtrationfiltered
9. 9
   Sonstigeevaporated

Vorschrift

(5-Phenyl-[1,2,3]triazolo[1,5-a]pyridin-3-yl)methanol . To a cooled (ice bath) suspension of lithium tetrahydroaluminate (0.0929 g, 2.45 mmol) in 2 mL THF (anhy) was added slowly a solution of methyl 5-phenyl-[1,2,3]triazolo[1,5-a]pyridine-3-carboxylate (0.310 g, 1.22 mmol) in 20 mL THF (internal temp remained <20 C). The mixture was allowed to stir in the ice bath 10 minutes. The mixture was diluted with EtOAc, washed with water, sat. NaHCO3, the organic layer dried over Na2SO4, and filtered. The aqueous layer still had uv activity so a solution of Rochelle's salt and EA were added and the mixture stirred 30 min. The organic layer was washed with sat NaHCO3, dried over Na2SO4, filtered, combined with main portion and evaporated. The title compound was isolated as a yellow solid.

Quelle