Triethylamine → 1-(4-Chlorophenyl)cyclopropanecarbaldehyde

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.

1. extractionextracted with chloroform
2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
3. concentrationconcentrated in vacuo
4. dissolutionThe obtained residue was dissolved in toluene (30 mL)
5. additionadded at −78° C. with a solution of diisobutylaluminum hydride in toluene (1.01 M, 4.35 mL)
6. stirringthe resultant was stirred at the same temperature for 1 hour
7. additionThe reaction solution was added with hydrochloric acid
8. extractionextracted with ethyl acetate
9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
10. concentrationconcentrated in vacuo
11. customThe obtained residue was purified

ORD record

ord-20c79873842b4fe38747a0ce833a06ce

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236789B2