Water → HCID 23117620, compound

Participants

Reaction Steps

Under argon flow, lithium aluminum hydride (78 g) was suspended in dehydrated tetrahydrofuran (1 L). Ethyl 2-(3,4-dichlorophenyl)-2-formylamino-4-pentenoate (334 g) in dehydrated tetrahydrofuran (1 L) was added to the suspension at room temperature, followed by refluxing for 15 minutes. After the mixture was cooled with ice, water (78 mL), 15% aqueous sodium hydroxide (78 mL), and then water (234 mL) were added to the mixture, and the resultant mixture was stirred at room temperature for one hour. The insoluble matter was passed through Celite, followed by washing with ethyl acetate. The filtrate was dried over magnesium sulfate anhydrate and concentrated under reduced pressure until the volume of the solution was decreased to 1 L. 4N HCl-1,4-dioxane (260 mL) was added to the residue, and the mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, followed by filtration and drying, to thereby give the title compound (260 g, 69%, 5 steps).

Provenance & Evidence