تفاعل #969895

معادلة التفاعل

hydrochloric acid

N-methylmorpholine

1-(4-methoxyphenyl)cyclopropane carboxylic acid

lithium aluminum hydride

→

1-(4-methoxyphenyl)cyclopropane carboaldehyde

المردود 84.0%

المذيبات

water

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGstirred at room temperature for 30 min
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   تجفيفThe organic layer was dried over anhydrous sodium sulfate
4. 4
   تركيزconcentrated in vacuo
5. 5
   workup.DISSOLUTIONThe obtained residue was dissolved in dichloromethane (15 mL)
6. 6
   workup.STIRRINGstirred at room temperature for 1.5 hours
7. 7
   ترشيحThe reaction solution was filtered
8. 8
   تركيزconcentrated in vacuo
9. 9
   أخرىThe obtained residue was purified

الإجراء التجريبي

Under an argon atmosphere, a solution of 1-(4-methoxyphenyl)cyclopropane carboxylic acid (2.00 g, 10.4 mmol) in tetrahydrofuran (20 mL) was added with lithium aluminum hydride (513 mg, 13.5 mmol) at 0° C., and the resultant was stirred at room temperature for 2 hours. The resultant was added sequentially with water and hydrochloric acid at 0° C., stirred at room temperature for 30 min and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was dissolved in dichloromethane (15 mL). The resultant was sequentially added with molecular sieves 4β (1.80 g), N-methylmorpholine (1.83 g, 15.6 mmol) and tetrapropylammonium perruthenate (1.83 mg, 0.520 mmol) at 0° C., and stirred at room temperature for 1.5 hours. The reaction solution was filtered using celite, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane:ethyl acetate=4:1), and 1-(4-methoxyphenyl)cyclopropane carboaldehyde (1.54 g, 84.0%) was obtained.

المصدر