Reaktion #7928

Reaktionsgleichung

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to room temperature
2. 2
   Sonstigethe reaction mixture was partitioned between EtOAc (500 mL) and water (500 mL)
3. 3
   WaschenThe EtOAc phase was washed with 0.8N HCl (500 mL), water (500 mL), 5% NaHCO3 (500 mL), and brine (200 mL)
4. 4
   Trocknendried with MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under vacuum to a brown oil (22.8 g)
7. 7
   SonstigeThis material was purified by column chromatography on EM silica gel 60 (230-400 mesh, 684 g)
8. 8
   Waschenas eluting solvent

Vorschrift

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.

Quelle