Dimethylformamide → HCID 86719446, compound

Participants

Reaction Conditions

Reaction Steps

THF (50 ml) was added to 4-{3-(triallylsilyl)propyl}phenylbromide (3) (14.2 g, 40.6 mmol) under a nitrogen atmosphere, the mixture was cooled to around −10° C. with brine ice, and a solution of 2 M iPrMgCl (0.70 equivalent amount, 14.2 ml) and a solution of 1.67 M nBuLi (1.4 equivalent amount, 34.0 ml) were respectively added dropwise. The mixture was stirred at around −10° C. for 2 hours, N,N-dimethylformamide (DMF) (2 equivalent amount, 6.3 ml) was then added, and the mixture was stirred at room temperature for 14 hours. Diethyl ether was added to the reaction mixture, and the mixture was neutralized with a saturated aqueous solution of ammonium chloride. The aqueous layer was extracted with diethyl ether, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under a reduced pressure to give a crude product. The crude product was purified by separating by silica gel column chromatography (elution solvent: hexane/ethyl acetate=20/1) to give 4-{3-(triallylsilyl)propyl}benzaldehyde (4) (yield amount: 11.0 g, yield: 89%), as shown in the following chemical reaction formula.

Provenance & Evidence