Reaktion #2042680

Reaktionsgleichung

2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) -1-butanone

vinyltriethoxysilane

→

brown oil

Ausbeute 100.0%

2-benzyl-2-dimethylamino-1-[2-(2-triethoxysilylethyl)-4-morpholinophenyl]-1-butanone

Ausbeute 100.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegased
2. 2
   TemperaturAfter heating for 29 hours
3. 3
   Temperaturat reflux
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   Sonstigethe product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate)

Vorschrift

14.6 g (40 mmol) of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl) -1-butanone, 750 mg (0.8 mmol) of RuH2 (CO) (PPh3)3 and 18.4 ml (88 mmol) of vinyltriethoxysilane were dissolved in 50 ml of toluene and degased using argon. After heating for 29 hours with stirring at reflux, the solvent was distilled off and the product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate). 22 g (100%) of a brown oil were obtained which were purified by boiling in heptane with active charcoal followed by filtration to give a yellow, viscous oil in a quantity of 20.6 g (95%). 1H-NMR (CDCl3): 0.64 ppm (3H, t, Bu-H4, 3JH,H =7.0 Hz); 1.10 ppm (2H, mc, Et-H2); 1.26 ppm (9H, t, CH3 of Si(OEt)3, 3JH,H =6.8 Hz); 1.88 ppm (2H, mc, Bu-H3); 2.36 ppm (6H, s, N(CH3)2); 2.72 ppm (2H, mc, Et-H1); 3.15 ppm (2H, mc, CH2 -Ph); 3.24 ppm (4H, mc, morpholine-N-CH2); 3.85 ppm (4H, mc, morpholine-o--CH2); 3.88 ppm (6H, q, SiOCH2); 6.60 ppm (1H, dd, Ph-H5, 3JH5,H6 =8.6 Hz, 4 JH3,H5 =2.6 Hz); 6.77 ppm (1H, d, Ph-H3); 7.12-7.28 ppm (5H, m, Ph'-H); 8.38 ppm (1H, d, Ph-H6).

Quelle