Reaktion #2042679

Reaktionsgleichung

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

vinyltrimethoxysilane

→

dark red oil

Ausbeute 67.0%

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

Ausbeute 67.0%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigedegased
2. 2
   TemperaturAfter heating
3. 3
   Temperaturat reflux for 41 hours
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   Sonstigethe product was chromatographed (silica gel, 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 13.4 ml (88 mmol) of vinyltrimethoxysilane were dissolved in 50 ml of toluene and degased using N2. After heating with stirring at reflux for 41 hours, the solvent was distilled off and the product was chromatographed (silica gel, CH2Cl2 /ethyl acetate). 13.8 g (67%) of dark red oil were obtained which were purified by boiling in heptane with active charcoal followed by filtration to give a yellow, viscous oil. 1H-NMR (CDCl3): 0.61 ppm (3H, t, Bu-H4, 3JH,H =7.2 Hz); 1.2 ppm (2H, mc, Et-H2); 1.88 ppm (2H, mc, Bu-H3); 2.37 ppm (6H, s, N(CH3)2); 2.71 ppm (2H, mc, Et-H1); 3.16 ppm (2H, mc, CH2 -Ph); 3.25 ppm (4H, mc, morpholine-N--CH2); 3.63 ppm (9H, s, Si(OCH3)3); 3.85 ppm (4H), mc, morpholine-O-CH2); 6.61 ppm (1H, dd, Ph-H5, 3JH5,H6, =8.6 Hz, 4 JH3, H6 =2.6 Hz); 6.75 ppm (1H, d, Ph-H3); 7.14-7.29 ppm (5H, m, Ph'-H); 8.44 ppm (1H, d, Ph-H6).

Quelle