반응 #155324

반응 방정식

1-bromo-3-chloropropane

DMF

8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

sodium hydride

→

6-(3-chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one

수율 92.0%

용매

ethyl acetate

Water

반응 조건

후처리

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   기타the resulting reaction mixture
3. 3
   기타was then subjected to separation
4. 4
   세척The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   건조After being dried over anhydrous sodium sulfate
6. 6
   농축the organic layer was concentrated under reduced pressure
7. 7
   기타The residue was purified
8. 8
   농축The purified product was concentrated under reduced pressure

실험 절차

To a DMF solution (6 ml) of 8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (1.26 g, 3.60 mmol) was added sodium hydride (60% oil base, 189 mg, 4.33 mmol). The mixture was stirred at room temperature for 10 minutes. To the resulting mixture was added 1-bromo-3-chloropropane (1.70 g, 10.8 mmol), followed by stirring at room temperature for 16 hours. Water and ethyl acetate were added to the reaction mixture and the resulting reaction mixture was then subjected to separation. The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice. After being dried over anhydrous sodium sulfate, the organic layer was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=20:1→12:1). The purified product was concentrated under reduced pressure, giving a yellow oily substance of 6-(3-chloropropyl)-8-(4-methoxyphenyl)-5-propoxy-1,2,3,6-tetrahydro-6-aza-cyclopenta[a]naphthalen-9-one (365 mg, yield: 92%).

출처