Reaktion #7919

Reaktionsgleichung

Potassium hydroxide

5-methoxy-1-indanone

butyraldehyde

→

2-butyl-5-methoxy-1-indanone

Ausbeute 104.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered
2. 2
   Sonstigethe filtrate evaporated under vacuum
3. 3
   SonstigeThe residue was partitioned between EtOAc (200 mL) and water (200 mL)
4. 4
   workup.ADDITIONcontaining 2N HCl (5 mL)
5. 5
   WaschenThe organic phase was washed with brine (100 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated under vacuum

Vorschrift

Potassium hydroxide (0.44 g, 85% weight pure, 6.67 mmol) and 10% palladium on activated carbon (0.42 g) were added to a mixture of 5-methoxy-1-indanone (5.0 g, 30.8 mmol) and butyraldehyde (3.3 mL, 37 mmol) in ethanol (30 mL). The resulting mixture was stirred under an atmosphere of hydrogen at room temperature for 2 hours. The mixture was filtered and the filtrate evaporated under vacuum. The residue was partitioned between EtOAc (200 mL) and water (200 mL) containing 2N HCl (5 mL). The organic phase was washed with brine (100 mL), dried over MgSO4, filtered, and evaporated under vacuum to afford crude 2-butyl-5-methoxy-1-indanone (7.0 g) as an oil.

Quelle