Reaction #969894

Reaction equation

1-(4-chlorophenyl)cyclopropane carboxylic acid

N,O-dimethylhydroxylamine hydrochloride

benzotriazole-1-yloxytrispyrrolidinophosphonium hexafluorophosphate

triethylamine

→

1-(4-chlorophenyl)cyclopropane carboaldehyde

Yield 63.8%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Extractionextracted with chloroform
2. 2
   DryingThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Concentrationconcentrated 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
   Extractionextracted with ethyl acetate
9. 9
   DryingThe organic layer was dried over anhydrous sodium sulfate
10. 10
    Concentrationconcentrated in vacuo
11. 11
    OtherThe obtained residue was purified

Procedure

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.

Source