Реакция #7928

Уравнение реакции

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

Условия реакции

Обработка

1. 1
   ТемператураAfter cooling to room temperature
2. 2
   Другоеthe reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL)
3. 3
   ПромывкаThe EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL)
4. 4
   Сушкаdried with MgSO4
5. 5
   Фильтрацияfiltered
6. 6
   Другоеevaporated under vacuum to a brown oil (22.8 g)
7. 7
   ДругоеThis material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g)
8. 8
   Промывкаas eluting solvent

Методика

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.

Источник