Hydrogen Cyanide → 2,2-Bis(trifluoromethyl)-4-(2-cyanoethyl)-4,5,5-trifluoro1,3-dioxolane

HRID 1195216

Reaktionsgleichung

[F:1][C:2]([F:18])([F:17])[C:3]1([C:13]([F:16])([F:15])[F:14])[O:7][C:6]([CH:9]=[CH2:10])([F:8])[C:5]([F:12])([F:11])[O:4]1.C([Al](Cl)Cl)C.[CH:24]#[N:25]>C1(C)C=CC=CC=1>[F:16][C:13]([F:14])([F:15])[C:3]1([C:2]([F:1])([F:17])[F:18])[O:7][C:6]([CH2:9][CH2:10][C:24]#[N:25])([F:8])[C:5]([F:11])([F:12])[O:4]1

Komponenten

Reaktionsbedingungen

Temperatur: 60 °C

Versuchsvorschrift

A mixture comprised of Ni[P(O-tolyl)3]4 (3.3 g, 2.2 mmole) and P(O-tolyl)3 (1.7 g, 4.8 mmole), 2,2-bis(trifluoromethyl)-4-vinyl-4,5,5-trifluoro-1,3-dioxolane (30 g, 0.103 mole), 25% EtAlCl2 in toluene (2.0 ml), and toluene (25 ml) was heated under nitrogen in an oil bath at 60° C. A 50% HCN in toluene solution was fed from an ISCO pump at a rate of 1.5 ml/hour for 4.5 hours and then 0.5 ml/hour overnight until the reaction was complete (GC determination). The mixture was allowed to cool and was purified by distillation to give 2,2- bis(trifluoromethyl)-4-(2-cyanoethyl)-4,5,5-trifluoro1,3-dioxolane as a clear, colorless liquid in 66% yield. Bp. 65°-68° C./7.0 mm. 1H-NMR (CDCl3): δ 2.72 (t, J=7.8 Hz, 2H), 2.50 (m, 2H); 19F NMR (CDCl3 ): -110.2 (m, 1F), -76.9, -77.6 (2m, 1F), -87.0, -87.7 (2d, J=9.3 Hz, 1F), -80.6 (m, 3F), -81.3 (m, 3F). Anal. Calc. for C8H4F9NO2 : C: 30.28, H: 1.27, F: 53.94; Found: 30.21, H: 1.34, F: 54.26. MS: [M]: Calc.: 317.0098; Found: 317.0081; MS (PCI): [M+H]: Calc.: 318.0177; Found: 318.0176. ##STR10##

Aufarbeitung

custom0.5 ml/hour overnight
temperatureto cool
distillationwas purified by distillation

Quellen und Nachweise

ORD-Eintrag: ord-77d5970b9b0c45e593876fb288acb509
Quelldatensatz: uspto-grants-1992_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05110938

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