Dimethylformamide → HCID 86719446, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, to 4-{3-(triallylsilyl)propyl}phenyl bromide (3) (14.2 g, 40.6 mmol), tetrahydrofuran (THF) (50 ml) was added, cooled to −10° C. using salt ice. 2M of iPrMgCl solution (0.70 equiv., 14.2 ml) and 1.67M of nBuLi solution (1.4 equiv., 34.0 ml) were each added dropwise, then stirred at around −10° C. for 2 hours. N,N-dimethylformamide (DMF) (2 equiv., 6.3 ml) was added and stirred at room temperature for 14 hours. To the reacted mixture, diethyl ether was added and then neutralized with saturated ammonium chloride aqueous solution. The obtained water layer was extracted with diethyl ether, the collected organic layer was washed with saturated saline solution then dried over anhydrous magnesium sulfate, then filtered and concentrated under reduced pressure, obtaining a crude product. The crude product was separated and purified using silica gel column chromatography (eluent: hexane/ethyl acetate=20/1), obtaining 4-{3-(triallylsilyl)propyl}benzaldehyde (4) represented by the following chemical formula (yield: 11.0 g, yield (%): 89%).

Provenance & Evidence