Dimethylformamide → 4-Cyclopropylbenzaldehyde

Temperature

-78 °C

To a solution of 4-bromostylene (1.83 g) in dichloromethane (5 mL) was added diethylzinc (1 mol/L, 30 mL) under an argon atmosphere at 0° C., and the mixture was stirred at the same temperature for 10 minutes. Chloroiodomethane (4.3 mL) was added to the mixture, and the mixture was warmed to room temperature and stirred for 9 days. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give 4-cyclopropylbromobenzene. The obtained 4-cyclopropylbromobenzene was dissolved in tetrahydrofuran (25 mL) and cooled to −78° C. To the solution was added dropwise tert-butyl lithium (1.45 mol/L pentane solution, 9.4 mL) under an argon atmosphere, and the mixture was stirred at −78° C. for 30 minutes. To the reaction mixture was added a solution of N,N-dimethylformamide (1.2 mL) in tetrahydrofuran (16 mL), and the mixture was warmed to 0° C. and stirred for 1 hour. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=12/1) to give 4-cyclopropylbenzaldehyde (0.72 g).

1. temperaturethe mixture was warmed to 0° C.
2. stirringstirred for 1 hour
3. extractionthe mixture was extracted with diethyl ether
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. customthe solvent was removed under reduced pressure
6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=12/1)

ORD record

ord-19e9a998f28946868815e06a318ccf88

Source dataset

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07087579B2