تفاعل #7973

معادلة التفاعل

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

المردود 29.1%

المذيبات

ethanol

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر