Reaktion #68460

Reaktionsgleichung

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

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

Lösungsmittel

ammonium hydroxide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction vessel was purged
2. 2
   Sonstigeflushed with nitrogen three times
3. 3
   SonstigeThe reaction mixture was microwaved at 150° C. for 60 minutes
4. 4
   FiltrationAfter 30 minutes the mixture was filtered
5. 5
   Sonstigethe filtrate was partitioned between water and ethyl acetate
6. 6
   ExtraktionExtracted with ethyl acetate (3×20 mL)
7. 7
   Waschenwashed with brine
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Einengenconcentrated
10. 10
    SonstigePurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

Vorschrift

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).

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