تفاعل #68460

معادلة التفاعل

4-chloro-7-methoxyquinoline

tri-t-butylphosphonium tetrafluoroborate

3-ethoxy-3-oxopropylzinc bromide

THF

→

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

المذيبات

ammonium hydroxide

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction vessel was purged
2. 2
   أخرىflushed with nitrogen three times
3. 3
   أخرىThe reaction mixture was microwaved at 150° C. for 60 minutes
4. 4
   ترشيحAfter 30 minutes the mixture was filtered
5. 5
   أخرىthe filtrate was partitioned between water and ethyl acetate
6. 6
   استخلاصExtracted with ethyl acetate (3×20 mL)
7. 7
   غسيلwashed with brine
8. 8
   تجفيفdried over magnesium sulfate
9. 9
   تركيزconcentrated
10. 10
    أخرىPurified by MPLC with a gradient of 20 to 50% EtOAc in CH2Cl2

الإجراء التجريبي

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).

المصدر