Reaktion #7973

Reaktionsgleichung

HCl

KOH

5-methoxy-3-propyl-1-indanone

(2-ethyl-[1,3]dioxolan-2-yl)acetaldehyde

→

2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanone

Ausbeute 29.1%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred vigorously at room temperature for 18 hours
2. 2
   Sonstigepartitioned between EtOAc (9 mL) and water (5 mL)
3. 3
   WaschenThe organic phase was washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated under vacuum to an oil (316 mg)
7. 7
   SonstigeThe crude product was purified by chromatography on a Biotage FLASH 12M column
8. 8
   Wascheneluting with 10% EtOAc in hexanes

Vorschrift

A mixture of 5-methoxy-3-propyl-1-indanone (184 mg, 0.90 mmol) and (2-ethyl-[1,3]dioxolan-2-yl)acetaldehyde (173 mg, 1.20 mmol) was treated with a solution of KOH (85% wt. pure, 20 mg, 0.30 mmol) in ethanol (1.0 mL). The resulting mixture was stirred at room temperature for 30 minutes, then treated with 10% Pd on carbon (9 mg), placed under a hydrogen atmosphere, and stirred vigorously at room temperature for 18 hours. The mixture was acidified with 2N HCl and partitioned between EtOAc (9 mL) and water (5 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and evaporated under vacuum to an oil (316 mg). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 2-[2-(2-ethyl-[1,3]dioxolan-2-yl)-ethyl]-5-methoxy-3-propyl-1-indanone (87 mg) as an oil.

Quelle