Hydrochloric Acid → 3-[(4,4,4-Trifluoro-3-oxo-1-butenyl)amino]-2-propenenitrile

Beteiligte Stoffe

Reaktionsschritte

Sodium hydride (60% dispersion in mineral oil, 400 mg, 10 mmol) was charged and washed with hexane twice. Into this flask, 1,2-dimethoxyethane (20 ml) was added and then a solution prepared by dissolving 4-amino-1,1,1-trifluoro-3-buten-2-one (1.4 g, 10 mmol) and 3-methoxyacrylonitrile (830 mg, 10 mmol) in 1,2-dimethoxyethane (5 ml) was added dropwise under ice-cooling. After stirring the mixture at room temperature for 4 hours, the reaction mixture was poured into water (50 ml). This mixture was acidified with concentrated hydrochloric acid under ice-cooling and then extracted with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (a eluting solvent: hexane/ethyl acetate=3/1 to 1/1) to obtain 593 mg (yield 31.2%) of title compound (IIa) having a low polarity and 680 mg (yield 35.8%) of title compound (IIb) having a high polarity.

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