반응 #2042680

반응 방정식

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

vinyltriethoxysilane

→

brown oil

수율 100.0%

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

수율 100.0%

용매

toluene

반응 조건

후처리

1. 1
   기타degased
2. 2
   온도After heating for 29 hours
3. 3
   온도at reflux
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   기타the product was chromatographed (silica gel, heptane/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 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).

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