Réaction #68460

Équation de réaction

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

Ethyl 3-(7-methoxyquinolin-4-yl)propanoate

Solvants

ammonium hydroxide

Conditions de réaction

Traitement

1. 1
   AutreThe reaction vessel was purged
2. 2
   Autreflushed with nitrogen three times
3. 3
   AutreThe reaction mixture was microwaved at 150° C. for 60 minutes
4. 4
   FiltrationAfter 30 minutes the mixture was filtered
5. 5
   Autrethe filtrate was partitioned between water and ethyl acetate
6. 6
   ExtractionExtracted with ethyl acetate (3×20 mL)
7. 7
   Lavagewashed with brine
8. 8
   Séchagedried over magnesium sulfate
9. 9
   Concentrationconcentrated
10. 10
    AutrePurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

Mode opératoire

4-chloro-7-methoxyquinoline (0.35 g, 2 mmol), tri-t-butylphosphonium tetrafluoroborate (0.05 g, 0.2 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.08 g, 0.09 mmol) were combined. The reaction vessel was purged and flushed with nitrogen three times, followed by addition of 3-ethoxy-3-oxopropylzinc bromide in THF (10 mL, 5 mmol, 0.5 M). The reaction mixture was microwaved at 150° C. for 60 minutes. Upon completion, ammonium hydroxide (10 mL) was added. After 30 minutes the mixture was filtered and the filtrate was partitioned between water and ethyl acetate. Extracted with ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried over magnesium sulfate, and concentrated. Purified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2. (ESI, pos. ion) m/z: 354.1 (M+H).

Source