Cesium fluoride → HCID 90203783, compound

Participants

Reaction Steps

To a solution of (E)-N-(1-(benzyloxy)propan-2-ylidene)-2-methylpropane-2-sulfinamide (CAN 393536-49-7, 3.1 g, 11.6 mmol) in dry THF (55 ml) under an argon atmosphere was added cesium fluoride (1.94 g, 12.8 mmol) followed by addition of trimethylsilyl cyanide (1.27 g, 1.71 ml, 12.8 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and poured into a separatory funnel. Organic phase was extracted with a 1M aqueous solution of sodium bicarbonate and the organic phase was collected. The aqueous phase was back-extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethyl acetate gradient to yield the title compound (2.53 gr, 74%); MS (ESI, m/z): 295.6 (M+H+).

Provenance & Evidence