Diisopropylamine → HCID 21801973, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 0.45 g (0.00448 mole) of diisopropylamine dissolved in 20 ml of tetrahydrofuran was added dropwise 2.6 ml (0.00448 mole) of n-butyl lithium (a 1.6M hexane solution) at 0° C., and the mixture was stirred for 20 minutes. After the mixture was cooled to -78° C., to the mixture was added dropwise a solution of 1.00 g (0.00448 mole) of 1-phenyl-3,4-dihydroquinolin-2 (1H)-one dissolved in 10 ml of tetrahydrofuran, and the mixture was stirred at the same temperature for 30 minutes. Next, to the mixture was added dropwise a solution of 2.06 g of di-t-butyl azodicarboxylate dissolved in 10 ml of tetrahydrofuran, and the mixture was stirred at -78° C. for one hour. After completion of the reaction, the reaction mixture was treated with an ammonium chloride aqueous solution, extracted with chloroform and dried over anhydrous sodium sulfate. Chloroform was removed under reduced pressure, and the residue was purified by silica gel column chromatography (eluent:ethyl acetate:hexane (1:5 v/v)) to obtain 1.41 g of the title compound as a colorless caramel-like product.

Provenance & Evidence