반응 #7973

반응 방정식

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

수율 29.1%

용매

ethanol

반응 조건

후처리

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

실험 절차

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.

출처