Acrolein → HCID 57426002, compound

Participants

Reaction Conditions

Reaction Steps

Into a dry round bottom flask containing the appropriate hydrazone (1.995 g, 6.35 mmol), 20 mL of TMEDA were added and, nitrogen was circulated through the reaction system. After the solution was cooled at −50° C., 10.2 mL of BuLi (2.5 M/hex, 25.5 mmol) were added and, the reaction mixture was stirred first at −50° C. for 40 minutes and then at room temperature for 35 minutes. After bubbling stopped, the flask was cooled at 0° C. and, 2.0 mL of acrolein (1.63 g, 29.1 mmol) were added. The reaction was stirred at 0° C. for 5 h, at which point, 30 mL of ice water were added. The product was extracted once from the aqueous phase with EtOAc and, the combined organic phase was washed 3 times with H2O and with brine. The organic phase was dried under Na2SO4 and, the solvent was removed under vacuum. After the product was purified by flash chromatography (10% EtOAc/90% hex), 0.1165 g (0.626 mmol) was obtained in a 10% yield.

Provenance & Evidence