Reaktion #57502

Reaktionsgleichung

sodium iodide

sodium methoxide

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

hexane ethyl acetate

sodium methoxide

→

required product

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

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturto reflux for a total of 10 hours
3. 3
   Temperaturcooled to ambient temperature
4. 4
   workup.WAITthen stored for 18 hours
5. 5
   Extraktionextracted with ethyl acetate (three times)
6. 6
   Waschenwashed with brine
7. 7
   Sonstigethen evaporated under reduced pressure
8. 8
   Sonstigeto give a yellow oil

Vorschrift

To a stirred solution of sodium methoxide (prepared from sodium, 0.014 g) in methanol (2 ml) at ambient temperature was added 2-(3,5-dichlorophenoxy)-N-(1-chloro-6-methylhept-4-yn-6-yl) butyramide (0.20 g) followed by further sodium methoxide (0.3 g) and sodium iodide (0.1 g). The mixture was stirred at ambient temperature under an atmosphere of nitrogen for 4 hours, heated to reflux for a total of 10 hours, cooled to ambient temperature then stored for 18 hours. The reaction mixture was diluted with water, extracted with ethyl acetate (three times) and the extracts were combined, washed with brine then evaporated under reduced pressure to give a yellow oil. The oil was fractionated by chromatography (silica; hexane/ethyl acetate, 3:1 by volume) to give the required product as a colourless oil, 0.055 g, 1H NMR (CDCl3) δ: 0.98-1.04(3H, t); 1.60(6H, s); 1.72-1.78(2H, m); 1.92-2.00(2H, m); 2.24-2.28((2H, t); 3.34(3H, s); 3.42-3.46(2H, t); 4.36-4.38(1H, t); 6.28(1H, s); 6.84(2H, s); 7.02(1H, s).

Quelle