Vinyltrimethoxysilane → HCID 19070342, Verbindung

HRID 1955495

Reaktionsgleichung

Reaktionsgleichung von HRID 1955495
[CH3:1][C:2]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:4].[CH:20]([Si:22]([O:27][CH3:28])([O:25][CH3:26])[O:23][CH3:24])=[CH2:21]>C1(C)C=CC=CC=1>[CH3:13][C:2]([N:14]1[CH2:15][CH2:16][O:17][CH2:18][CH2:19]1)([CH3:1])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][C:6]=1[CH2:21][CH2:20][Si:22]([O:27][CH3:28])([O:25][CH3:26])[O:23][CH3:24])=[O:4]

Komponenten

4

Edukt 2

HCID 76004VinyltrimethoxysilaneHCID 923872-Methyl-1-(4-(methylthio)phenyl)-2-morpholino-1-propanone

Produkt 1

HCID 19070342HCID 19070342, VerbindungAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureat reflux for 5 hours
  2. waitboiling was repeated for 4 hours
  3. temperatureat reflux for a further 5 hours
  4. concentrationConcentration and chromatography (silica gel, CH2Cl2 /ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-71ee16c1c3fc40adbe415da44ff31e07
Quelldatensatz
uspto-grants-1998_07
Patentnummer
US05776658

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