反应 #155327

反应方程式

Ethyl bromoacetate

Sodium hydride

DMF

3-(4-methoxyphenyl)-10-propoxy-1,6,7,8-tetrahydro-5-oxa-1-aza-phenanthren-4-one

→

ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate

收率 95.0%

溶剂

ethyl acetate

Water

反应条件

后处理

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 16 hours
2. 2
   其他followed by separation
3. 3
   洗涤The thus-obtained organic layer was washed with water
4. 4
   干燥dried over anhydrous sodium sulfate
5. 5
   浓缩concentrated under reduced pressure
6. 6
   其他The residue was purified
7. 7
   浓缩The purified product was concentrated under reduced pressure

实验过程

Sodium hydride (60% oil base, 80 mg, 2.0 mmol) was added to a DMF solution (10 ml) of 3-(4-methoxyphenyl)-10-propoxy-1,6,7,8-tetrahydro-5-oxa-1-aza-phenanthren-4-one (600 mg, 1.64 mmol), the resulting mixture was then stirred at room temperature for 5 minutes. Ethyl bromoacetate (330 mg, 2.0 mmol) was added thereto and the resulting mixture was stirred at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture, followed by separation. The thus-obtained organic layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified using medium pressure liquid chromatography (NH silica gel, n-hexane:ethyl acetate=100:0→0:100). The purified product was concentrated under reduced pressure, giving a colorless oily substance ethyl[3-(4-methoxyphenyl)-4-oxo-10-propoxy-7,8-dihydro-4H,6H-5-oxa-1-aza-phenanthren-1-yl]acetate (700 mg, yield: 95%).

来源