Dimethylformamide → 8-Formyl-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

Participants

Reaction Conditions

Reaction Steps

To a solution of 8-bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene (1.68 gm, 5.4 mMol) in tetrahydrofuran (50 mL) at -78° C. was added a solution of n-butyl lithium in hexane (1.6 M, 5.4 mL, 8.6 mMol), and the solution was stirred for one hour at -78° C. To the solution was then added N,N-dimethylformamide (0.3 mL, 5.94 mMol), and the reaction mixture was allowed to warm gradually to room temperature. The reaction mixture was diluted with water (10 mL) and stirred vigorously for one-half hour. The reaction mixture was then extracted with chloroform. The combined extracts were washed with saturated aqueous sodium chloride, dried over sodium sulfate and evaporated in vacuo to give a yellow-green oil. Purification by flash chromatography (3% methanol in dichloromethane+tr. NH4OH) gave the title compound as a colorless oil (700 mg, 50%). The maleate salt was formed and crystallized (ethanol/diethyl ether) to give colorless crystals (m.p.=120°-121° C.).

Provenance & Evidence