反応 #7928

反応方程式

solution

2-butyl-5-methoxy-2-(3-oxo-butyl)-1-indanone

pyrrolidine

acetic acid

→

9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one

反応条件

後処理

1. 1
   温度After cooling to room temperature
2. 2
   その他the reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL)
3. 3
   洗浄The EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL)
4. 4
   乾燥dried with MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated under vacuum to a brown oil (22.8 g)
7. 7
   その他This material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g)
8. 8
   洗浄as eluting solvent

実験手順

The solution from step 2 was treated with pyrrolidine (6.9 mL, 82 mmol) and acetic acid (4.7 mL, 82 mmol), placed under a nitrogen atmosphere, and stirred with heating in a 60° C. bath for 22 hours. After cooling to room temperature, the reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL). The EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL), dried with MgSO4, filtered, and evaporated under vacuum to a brown oil (22.8 g). This material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g), using 5% EtOAc in CH2Cl2 as eluting solvent, to afford 9a-butyl-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one (11.2 g) as a solid.

出典