Reacción #7973

Ecuación de reacción

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

Rendimiento 29.1%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente