Toluene → HCID 24941074, compound

Participants

Reaction Steps

A solution of (±)-2 -cyanomethylene-N-methyl-1-(pyrid-3 -yl}cyclohexane carbothioamide (1.3 g, 4.8 mmol) in dichloromethane (30 ml) was cooled to -20° C. and treated with a 1 M solution of diisobutylaluminium hydride in toluene (10.6 ml, 10.6 mmol). The mixture was allowed to warm to room temperature over 2 hours. Dichloromethane (50 ml) was added to the reaction mixture followed by an aqueous solution of Rochelle salt (sodium potassium tartrate) (50 ml). The layers were separated and the organic layer was washed with an aqueous solution of Rochelle salt (50 ml). The organic extract was dried over magnesium sulphate and concentrated in vacuo to give a crude gum which was purified by flash chromatography over silica gel, eluting with a 4:1 (v/v) mixture of ethyl acetate/hexane to give (±)-2 -formylmethylene-N-methyl-1-(pyrid-3 -yl)cyclohexane carbothioamide as a white foam (230 mg, 0.84 mmol);

Provenance & Evidence