Malonic Acid → HCID 23360158, compound

Participants

Reaction Steps

Into a mixture of 0.946 g of sodium borohydride and 100 ml of tetrahydrofuran, a mixed solution of 2.850 g of trifluoroacetic acid and 20 ml of tetrahydrofuran, was dropwise added under stirring and cooling with ice. After the completion of the dropwise addition, the ice bath was removed, and the reaction mixture was stirred for one hour. Then, a solution obtained by dissolving 4.325 g of 4-cyanociannamic acid obtained by heating and condensing 4-cyanobenzaldehyde with malonic acid in pyridine in the presence of a catalytic amount of piperidine, in 140 ml of tetrahydrofuran and 30 ml of 1,4-dioxane, was dropwise added to the reaction mixture, and stirred at room temperature for 2.5 hours. After cooling, ice pieces were added to decompose the excess reducing agent. Then, the reaction mixture was concentrated, and the precipitated powder was collected by filtration and subjected to vacuum drying to obtain 3.50 g of the above identified compound as a colorless powder.

Provenance & Evidence