반응 #2042681

반응 방정식

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

allyltrimethoxysilane

toluene

→

( 11 )

수율 4.0%

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

수율 4.0%

반응 조건

후처리

1. 1
   기타degased with argon
2. 2
   온도After heating for 5 hours
3. 3
   온도at reflux
4. 4
   workup.WAITthe mixture was left
5. 5
   workup.STIRRINGstirred
6. 6
   온도at reflux for a further 9 hours
7. 7
   workup.WAITagain left
8. 8
   기타to stand at room temperature
9. 9
   workup.WAITthe mixture was boiled for 9 hours
10. 10
    workup.WAITit was then again left
11. 11
    workup.WAITto stand overnight
12. 12
    workup.WAITthe whole mixture was boiled again for 9 hours
13. 13
    workup.DISTILLATIONAfter the solvent had been distilled off
14. 14
    기타the product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate)

실험 절차

5.49 g (15 mmol) of 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-1-butanone, 275 mg (0.3 mmol) of RuH2 (CO) (PPh3)3 and 5 g (30 mmol) of allyltrimethoxysilane were dissolved in 20 ml of toluene and degased with argon. After heating for 5 hours at reflux with stirring, the mixture was left to stand overnight, stirred at reflux for a further 9 hours, and again left to stand at room temperature. 280 mg (0.3 mmol) of RuH2 (CO) (PPh3)3 were added and the mixture was boiled for 9 hours; it was then again left to stand overnight, 260 mg (0.3 mmol) of RuH2 (CO)(PPh3)3 were added, and the whole mixture was boiled again for 9 hours. After the solvent had been distilled off, the product was chromatographed (silica gel, heptane/CH2Cl2 /ethyl acetate) and finally, by means of gel permeation chromatography (Sephadex LH-20, methanol) a pure fraction of 0.33 g (4%) of (11) was obtained as a yellow oil. 1H-NMR (CDCl3): 0.68 ppm (3H, t, Bu-H4, 3 JH,H =7.2 Hz); 0.77 ppm (mc, 2H, Prop-H3); 1.64-1.96 ppm (4H, m, Bu-H3 and Prop-H2); 2.38 ppm (6H, s, N(CH3)2); 2.64 ppm (2H, mc, Prop-H1); 3.16 ppm (2H, mc, CH2 -Ph); 3.24 ppm (4H, mc, morpholine-N --CH2); 3.57 ppm (9H, s, Si(OCH3)3); 3.85 ppm (4H, mc morpholine-O-CH2); 6.61 ppm (1H, dd, Ph-H5, 3 JH5H,6 =8.6 Hz); 6.72 ppm (1H, d, Ph-H3, 4JH3,H5 =2.4 Hz); 7.13-7.25 ppm (5H, m, Ph'-H); 8.38 ppm (1H, d, Ph-H6).

출처