Acetic Acid → 4-(2-Cyano-3-oxobut-1-en-1-yl)-3-(methylsulfonyl)benzonitrile

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Reaction Steps

4-Formyl-3-(methylsulfonyl)benzonitrile (3.0 g, 14.34 mmol) and sodium 1-cyanoprop-1-en-2-oxide (1.66 g, 15.8 mmol, 1.1 eq.; cf. R. Troschtitz, Archiv der Pharmazie 1984, 317, 709-713) were initially charged in dichloromethane (180 ml). Glacial acetic acid (1.03 ml, 18 mmol, 1.25 eq.) and piperidine (142 μl, 1.43 mmol, 0.1 eq.) were then added, and the mixture was heated under reflux on a water separator (18 h). The reaction solution was then washed once with water (50 ml) and twice with saturated sodium bicarbonate solution (100 ml each), dried over sodium sulfate and concentrated. The solid residue was suspended in six times the amount of ethanol and once more filtered off with suction, and the crystals were washed with ethanol and dried under high vacuum. This gave 2.7 g (70% pure, 48% of theory) of the title compound.

Provenance & Evidence