Reaktion #57503

Reaktionsgleichung

hexane ethyl acetate

1,2,4-triazole

2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide

potassium carbonate

→

required product

2-(3,5-dichlorophenoxy)-N-(6-methyl-1-(1,2,4-triazol-1-yl)-hept-4-yn-6-yl) butyramide

Lösungsmittel

water

ethyl acetate

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to ambient temperature
2. 2
   Extraktionextracted with ethyl acetate (three times)
3. 3
   Waschenwashed with brine
4. 4
   Trocknendried over magnesium sulphate
5. 5
   Sonstigethen evaporated under reduced pressure
6. 6
   Sonstigeto give a yellow oil

Vorschrift

To a stirred solution of 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (0.59 g) in dry N,N-dimethylformamide (10 ml) containing anhydrous potassium carbonate (0.28 g) was added 1,2,4-triazole (0.10 g). The mixture was heated to 90° C. for 2.75 hours, cooled to ambient temperature, diluted with water and extracted with ethyl acetate (three times). The extracts were combined, washed with brine, dried over magnesium sulphate then evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 2:1 by volume followed by ethyl acetate) to give the required product as a colourless oil, 0.16 g, 1H NMR (CDCl3) δ: 1.00-1.06(3H, t); 1.60(3H, s); 1.62(3H, s); 1.92-2.14(6H, m); 4.38-4.44(3H, m); 6.26(1H, s); 6.84(2H, s); 7.04(1H, s); 7.96(1H, s); 8.32(1H, s).

Quelle