반응 #2042679

반응 방정식

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

vinyltrimethoxysilane

→

dark red oil

수율 67.0%

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

수율 67.0%

용매

toluene

반응 조건

후처리

1. 1
   기타degased
2. 2
   온도After heating
3. 3
   온도at reflux for 41 hours
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   기타the product was chromatographed (silica gel, CH2Cl2 /ethyl acetate)

실험 절차

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).

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