Reaktion #720948

Reaktionsgleichung

NaOH

methyl quinoline-5-carboxylate

lithium aluminum hydride

H2O

H2O

→

Quinolin-5-ylmethanol

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe precipitate formed
2. 2
   Filtrationis filtered off
3. 3
   Waschenwashed with THF
4. 4
   WaschenThe organic phase is washed with saturated NaCl solution
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated
7. 7
   SonstigeAfter purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol
8. 8
   Sonstigeare obtained, corresponding to the following characteristics

Vorschrift

A suspension of 171 mg (4.49 mmol) of lithium aluminum hydride in 20 ml of THF is cooled to 0° C. A solution of 700 mg (3.74 mmol) of methyl quinoline-5-carboxylate in 5 ml of THF is then added dropwise. The reaction mixture is stirred at 0° C. for 1 hour and then hydrolysed with, in this order, 0.17 ml of H2O, 0.17 ml of NaOH and 3×0.17 ml of H2O. The precipitate formed is filtered off and washed with THF and then with EtOAc. The organic phase is washed with saturated NaCl solution, dried and evaporated. After purification by chromatography on silica gel (eluent: 95/5 DCM/MeOH), 190 mg of quinolin-5-ylmethanol are obtained, corresponding to the following characteristics:

Quelle