反応 #7936

反応方程式

9a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

cesium carbonate

1-(2-chloroethyl)-piperidine monohydrochloride

→

9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one

収率 96.3%

溶媒

acetone

EtOAc

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   ろ過filtered
3. 3
   その他to remove salts
4. 4
   洗浄The filtrate was washed with water and brine
5. 5
   乾燥dried over MgSO4
6. 6
   ろ過filtered
7. 7
   その他evaporated under vacuum to a yellow gum (0.95 g)
8. 8
   その他The crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 50 mL dry)
9. 9
   洗浄as eluting solvent
10. 10
    workup.ADDITIONThe product containing fractions
11. 11
    その他were evaporated under vacuum

実験手順

A mixture of crude 9a-butyl-4-(4-hydroxyphenyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (787 mg, approx. 2 mmol), cesium carbonate (1.564 g, 4.8 mmol), and 1-(2-chloroethyl)-piperidine monohydrochloride (442 mg, 2.4 mmol) in acetone (5 mL) was stirred and heated in an oil bath at 60° C. for 4 hours. After cooling to room temperature, the mixture was diluted with EtOAc and filtered to remove salts. The filtrate was washed with water and brine, dried over MgSO4, filtered, and evaporated under vacuum to a yellow gum (0.95 g). The crude product was purified by chromatography on EM silica gel 60 (230-400 mesh, 50 mL dry) using 2% MeOH+1% Et3N in EtOAc as eluting solvent. The product containing fractions were evaporated under vacuum and the residue stripped with toluene to provide 9a-butyl-7-methoxy-4-{4-[2-(1-piperidinyl)ethoxy]phenyl}-1,2,9,9a-tetrahydro-3H-fluoren-3-one (912 mg, 96% weight pure) as a pale yellow gum.

出典