Vinyltrimethoxysilane → 2-Methyl-1-[4-methylthio-2-(2-trimethoxysilylethyl)phenyl]-2-morpholino-1-propanone

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Reaction Steps

11.18 g (40 mmol) of 2-methyl-1-(4-methylthiophenyl)-2-morpholino-1-propanone, 735 mg (0.8 mmol) of RuH2 (CO)(PPh3)3 and 7.3 ml (48 mmol) of vinyltr 60 ml of anhydrous toluene were degased with argon for 1/2 hour and boiled at reflux for 5 hours. After standing overnight, boiling was repeated for 4 hours, then 360 mg (0.4 mmol) of RuH2 (CO)(PPh3)3 and 2 ml (13 mmol) of vinyltrimethoxysilane were added, and the mixture was stirred at reflux for a further 5 hours. Concentration and chromatography (silica gel, CH2Cl2 /ethyl acetate) gave 3.04 g (18%) of a yellowish oil. 1H-NMR (CDCl3): 1.01 ppm (2H, mc, Et-H2); 1.22 ppm (6H, s, Pr-H3, CH3); 2.50 ppm (3H, s, -SCH3); 2.58 ppm (4H, mc, *morpholine--O--CH2); 2.69 ppm (2H, mc, Et-H1); 3.59 ppm (9H, s, Si(OCH3)3); 3.70 ppm (4H, mc, **morpholine--N--CH2); 7.03 ppm (1H, dd, Ph-H5, 3 JH5, H6 =8.4 Hz, 4JH3,h5 =2.0 Hz); 7.11 ppm (1H, d, Ph-H3); 8.47 ppm (1H, d, Ph-H6).

Provenance & Evidence