反応 #155324

反応方程式

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

収率 92.0%

溶媒

ethyl acetate

Water

反応条件

後処理

1. 1
   workup.STIRRINGby stirring at room temperature for 16 hours
2. 2
   その他the resulting reaction mixture
3. 3
   その他was then subjected to separation
4. 4
   洗浄The thus-obtained organic layer was washed with an aqueous saturated sodium chloride solution twice
5. 5
   乾燥After being dried over anhydrous sodium sulfate
6. 6
   濃縮the organic layer was concentrated under reduced pressure
7. 7
   その他The residue was purified
8. 8
   濃縮The purified product was concentrated under reduced pressure

実験手順

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%).

出典