反応 #7973

反応方程式

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

収率 29.1%

溶媒

ethanol

反応条件

後処理

1. 1
   workup.STIRRINGstirred vigorously at room temperature for 18 hours
2. 2
   その他partitioned between EtOAc (9 mL) and water (5 mL)
3. 3
   洗浄The organic phase was washed with brine
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   その他evaporated under vacuum to an oil (316 mg)
7. 7
   その他The crude product was purified by chromatography on a Biotage FLASH 12M column
8. 8
   洗浄eluting with 10% EtOAc in hexanes

実験手順

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.

出典