Toluene → ethyl (2E)-2-(benzylhydrazinylidene)acetate

Participants

Reaction Steps

47% ethyl glyoxylate in toluene (polymer type) (29.2 g, 134.5 mmol) was dissolved in THF (200 ml), and to the solution was added benzylhydrazine monohydrochloride (21.3 g, 134.5 mmol) and triethylamine (20.6 ml, 148 mmol), and stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, washed with water, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 14.9 g of E-ethyl 2-(2-benzylhydrazono)acetate (mixture of E:Z=4:1) (yield: 53%) as oil.

Provenance & Evidence