반응 #155327

반응 방정식

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

수율 95.0%

용매

ethyl acetate

Water

반응 조건

후처리

1. 1
   workup.STIRRINGthe resulting mixture was stirred at room temperature for 16 hours
2. 2
   기타followed by separation
3. 3
   세척The thus-obtained organic layer was washed with water
4. 4
   건조dried over anhydrous sodium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified
7. 7
   농축The purified product was concentrated under reduced pressure

실험 절차

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%).

출처