反応 #68460

反応方程式

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

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

溶媒

ammonium hydroxide

反応条件

後処理

1. 1
   その他The reaction vessel was purged
2. 2
   その他flushed with nitrogen three times
3. 3
   その他The reaction mixture was microwaved at 150° C. for 60 minutes
4. 4
   ろ過After 30 minutes the mixture was filtered
5. 5
   その他the filtrate was partitioned between water and ethyl acetate
6. 6
   抽出Extracted with ethyl acetate (3×20 mL)
7. 7
   洗浄washed with brine
8. 8
   乾燥dried over magnesium sulfate
9. 9
   濃縮concentrated
10. 10
    その他Purified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

実験手順

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).

出典