Water → HCID 68849591, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (3.91) in dry N,N-dimethylformamide (35 ml) containing potassium cyanide (0.78 g) was heated to 95° C. for 6 hours, cooled to ambient temperature then stored for 18 hours. The mixture was poured into water, extracted with diethyl ether (three times) and the extracts were combined, washed with water (three times), dried over magnesium sulphate then evaporated under reduced pressure to give the required product as a yellow oil, 3.42 g. A portion of this material was fractionated by chromatography (silica; hexane/ethyl acetate 3:1 by volume) to give a pure sample of 2-(3,5-dichlorophenoxy)-N-(1-cyano-6-methylhept-4-yn-6-yl) butyramide as a yellow gum, 1H NMR (CDCl3) δ: 0.98-1.02(3H, t); 1.58(3H, s); 1.60(3H, s); 1.82-1.88(2H, m); 1.92-1.98(2H, m); 2.36-2.40(2H, t); 2.48-2.56(2H, m); 4.38-4.42(1H, t); 6.26(1H, s); 6.84(2H, s); 7.04(1H, s).

Provenance & Evidence