反応 #969894

反応方程式

1-(4-chlorophenyl)cyclopropane carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphate

triethylamine

→

1-(4-chlorophenyl)cyclopropane carboaldehyde

収率 63.8%

溶媒

dichloromethane

反応条件

後処理

1. 1
   抽出extracted with chloroform
2. 2
   乾燥The organic layer was dried over anhydrous sodium sulfate
3. 3
   濃縮concentrated in vacuo
4. 4
   workup.DISSOLUTIONThe obtained residue was dissolved in toluene (30 mL)
5. 5
   workup.ADDITIONadded at −78° C. with a solution of diisobutylaluminum hydride in toluene (1.01 M, 4.35 mL)
6. 6
   workup.STIRRINGthe resultant was stirred at the same temperature for 1 hour
7. 7
   workup.ADDITIONThe reaction solution was added with hydrochloric acid
8. 8
   抽出extracted with ethyl acetate
9. 9
   乾燥The organic layer was dried over anhydrous sodium sulfate
10. 10
    濃縮concentrated in vacuo
11. 11
    その他The obtained residue was purified

実験手順

A solution of 1-(4-chlorophenyl)cyclopropane carboxylic acid (784 mg, 3.99 mmol) in dichloromethane (30 mL) was added sequentially at room temperature with N,O-dimethylhydroxylamine hydrochloride (389 mg, 3.99 mmol), benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphate (2.28 g, 4.39 mmol) and triethylamine (807 mg, 7.97 mmol). The resultant was stirred at the same temperature for 20 min, and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was dissolved in toluene (30 mL), added at −78° C. with a solution of diisobutylaluminum hydride in toluene (1.01 M, 4.35 mL), and the resultant was stirred at the same temperature for 1 hour. The reaction solution was added with hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified using column chromatography (hexane:ethyl acetate=3:1), and 1-(4-chlorophenyl)cyclopropane carboaldehyde (460 mg, 63.7%) was obtained.

出典