反応 #969895

反応方程式

hydrochloric acid

N-methylmorpholine

1-(4-methoxyphenyl)cyclopropane carboxylic acid

lithium aluminum hydride

→

1-(4-methoxyphenyl)cyclopropane carboaldehyde

収率 84.0%

溶媒

water

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGstirred at room temperature for 30 min
2. 2
   抽出extracted with ethyl acetate
3. 3
   乾燥The organic layer was dried over anhydrous sodium sulfate
4. 4
   濃縮concentrated 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
   ろ過The reaction solution was filtered
8. 8
   濃縮concentrated in vacuo
9. 9
   その他The obtained residue was purified

実験手順

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.

出典