Reaktion #823861

Reaktionsgleichung

4-Bromo-2-methylquinoline

methyl 4-formylbenzoate

lithium

n-BuLi

→

methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate

Ausbeute 65.0%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting solution was maintained at −78° C. for 5 min
2. 2
   Sonstigequenched with MeOH
3. 3
   workup.ADDITIONThe solution was diluted with ethyl acetate
4. 4
   Waschenwashed with H2O and brine
5. 5
   TrocknenAfter dried over MgSO4
6. 6
   Filtrationthe organic solution was filtered
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was purified on silica gel

Vorschrift

4-Bromo-2-methylquinoline from (4a) (1.0 g, 4.5 mmol) was dissolved in 10 mL of anhydrous THF and the resulting solution was cooled to -78° C. A solution of n-BuLi (3.0 mL, 1.6 M, 4.8 mmol) was added slowly and the resulting solution was maintained at −78° C. for 5 min. Meanwhile, in another flask methyl 4-formylbenzoate (0.9 g, 5.4 mmol) was dissolved in 20 mL of anhydrous THF and the resulting solution was cooled to −78° C. before the lithium reagent made above was cannulated. The whole mixture was stirred for 30 min and quenched with MeOH. The solution was diluted with ethyl acetate and washed with H2O and brine. After dried over MgSO4, the organic solution was filtered and concentrated. The residue was purified on silica gel to provide methyl 4-[hydroxy(2-methyl-4-quinolinyl)methyl]benzoate (0.9 g, 65%). MS (AP+): 308 (M+1).

Quelle