2-Propanesulfonyl chloride → alpha-(2-Propylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide

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Reaction Steps

As described under 1.2, 16.5 g (0.08 mol) of α-hydroxyimino-3,4-dimethoxybenzyl cyanide are reacted with 12.6 g (0.088 mol) of 2-propanesulfonyl chloride in the presence of triethylamine. Recrystallisation of the crude product from ethyl acetate/hexane yields 21.9 g (88%) of α-(2-propylsulfonyloxyimino)-3,4-dimethoxybenzyl cyanide in the form of beige crystals having a melting point of 90.5-93.5° C. The 1H-NMR spectrum of the compound shows that it is a pure stereoisomer. The UV spectrum (acetonitrile) of the substance shows a broad absorption band with a maximum at 346 nm (ε=1165034) that extends to 434 nm. Elemental analysis: C13H16N2O5S (312.34)

Provenance & Evidence