Reaktion #638306

Reaktionsgleichung

2-(3-bromo-phenyl)-5-methyl-thiophene

n-butyllithium

cyclohexane

[8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde

→

final product

Ausbeute 46.0%

2-[8-(Benzyloxy)-5-chloroquinolin-7-yl]-1-[3-(5-methyl-2-thienyl)phenyl]ethanol

Ausbeute 46.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGStirring at −78° C.
2. 2
   workup.WAITwas continued for 10 min
3. 3
   Temperaturto warm to room temperature
4. 4
   workup.STIRRINGwas stirred 1 h
5. 5
   SonstigeThe reaction mixture was then quenched with saturated aqueous ammonium chloride solution (10 mL)
6. 6
   Extraktionextracted with ethyl acetate (3×10 mL)
7. 7
   TrocknenThe combined organic layers were dried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated
10. 10
    Sonstigeto give a yellow oil that
11. 11
    Sonstigewas purified by column chromatography

Vorschrift

To a stirring solution of 2-(3-bromo-phenyl)-5-methyl-thiophene (0.395 mmol) in tetrahydrofuran (4 mL) at −78° C. was slowly added a 2M solution of n-butyllithium in cyclohexane (0.435 mmol, 1.1 eq.). The resulting solution was stirred 30 min at −78° C. and solid [8-(benzyloxy)-5-chloroquinolin-7-yl]acetaldehyde (0.395 mmol) was added. Stirring at −78° C. was continued for 10 min and the reaction was allowed to warm to room temperature and was stirred 1 h. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (10 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to give a yellow oil that was purified by column chromatography using 20% ethyl acetate/hexanes to give the final product as a light yellow solid (0.18 mmol, 46%). MS (ESI) m/z 486.4.

Quelle