反应 #68460

反应方程式

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

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

溶剂

ammonium hydroxide

反应条件

后处理

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

实验过程

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).

来源