Reaktion #1925226

Reaktionsgleichung

1-(butyl)-3-(3-triethoxysilylpropyl)-4,5-dihydroimidazolium chloride

sodium tetrafluoroborate

→

complex ( 3 )

Ausbeute 99.0%

1-(butyl)-3-(3-triethoxysilylpropyl)-4,5-dihydroimidazolium tetrafluoroborate

Ausbeute 99.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter the removal of the precipitate
2. 2
   Filtrationby filtration the volatiles
3. 3
   Sonstigewere evaporated under reduced pressure (10−2 torr)

Vorschrift

The complex 1-(butyl)-3-(3-triethoxysilylpropyl)-4,5-dihydroimidazolium chloride (2) (10 g, 28.0 mmol) was dissolved in acetonitrile (200 ml) and treated with one equivalent of sodium tetrafluoroborate (3.1 g, 28.0 mmol). The resulting slurry was stirred for 5 days at room temperature. After the removal of the precipitate by filtration the volatiles were evaporated under reduced pressure (10−2 torr) to give a brown liquid of complex (3) in 99% yield. 1H NMR (CD3CN) 0.50 (m, 2H, 3J=7.0, CH2—CH2—Si), 0.86 (tr, 3H, 3J=7.4, —CH2—CH2—CH3), 1.11 (tr, 9H, 3J=7.0, CH3—CH2—O), 1.26 (six, 2H, 3J=7.4, —CH2—CH2—CH3), 1.54 (m, 2H, Si—CH2—CH2—), 1.62 (m, 2H, —CH2—CH2—CH3), 3.38 (m, 4H, Si—CH2—CH2—CH2—N and —N—CH2—CH2—N—Bu), 3.72 (qr, 6H, CH3—CH2—O), 4.84 (m, 4H, —N—CH2—CH2—CH2—CH3 and —N—CH2—CH2—N—Bu), 8.20 (s, 1H, N—CH—N) ppm; 13C NMR (CD3CN) 8.47 (1C, Si—CH2—CH2—)−, 14.81 (1C, —CH2—CH2—CH3), 19.53 (3C, CH3—CH2—O—), 20.98 (1C, —CH2—CH2—CH3), 22.44 (1C, Si—CH2—CH2—), 30.54 (1C, —CH2—CH2—CH3), 49.09, 49.73, 49.89, 51.58 (4C, —CH2—N—CH2—CH2—N—CH2—), 59.90 (3C, CH3—CH2—O—), 159.09 (1C, N—CH—N) ppm; FT-IR (KBr) 3087 w, 2973 s, 2929 s, 2880 s, 1658 s, 1524 m, 1449 m, 1388 s, 1303 m, 1255 m, 1080 br, 957 m, 787 s cm−1; MS/ES+ (m/e) 331 [M+]. Anal. Calcd. for C16H35N2BF4O3Si: C, 45.94; H, 8.43; N, 6.70; B, 2.58; F, 18.16. Found: C, 45.95; H, 8.52; N, 7.34; B, 2.24; F, 17.86.

Quelle