Ethyl Acetate → HCID 54056685, compound

Participants

Reaction Steps

A solution of diethyl cyanomethylphosphonate (215 mg, 1.2 mmol) at room temperature in dry tetrahydrofuran (20 ml) was treated with a 60% oil dispersion of sodium hydride (40 mg, 1 mmol). After 15 mins at room temperature (±)-N-methyl-2-oxo-1-(pyrid-3-yl)cyclohexane carbothioamide (245 mg, 1 mmol) was added and the resulting solution stirred for 3 hours at room temperature. Ethyl acetate (50 ml) and then water (50 ml) were added to the reaction mixture. The layers were separated and the organics washed with water (50 ml). The organic extract was dried over magnesium sulphate and concentrated in vacuo to give a crude gum. Purification by flash chromatography, eluting with a 1:1 (v/v) mixture of ethyl acetate/hexane gave (±)-2-cyanomethylene-N-methyl-1-(pyrid-3-yl)cyclohexane carbothioamide as a colourless gum (190 mg, 0.7 mmol). Trituration with ether yielded a white solid (190 mg, 0.7 mmol), m.p. 182°183° C.;

Provenance & Evidence