Vinylene carbonate → HCID 14271043, Verbindung

HRID 1295490

Reaktionsgleichung

Reaktionsgleichung von HRID 1295490
[CH3:1][O:2][C:3]1([O:12][CH3:13])[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]1[Cl:11].[C:14]1(=[O:19])[O:18][CH:17]=[CH:16][O:15]1>>[Cl:11][C:4]12[C:3]([O:2][CH3:1])([O:12][CH3:13])[C:7]([Cl:8])([C:6]([Cl:9])=[C:5]1[Cl:10])[CH:17]1[CH:16]2[O:15][C:14](=[O:19])[O:18]1

Komponenten

3

Edukt 2

HCID 13385Vinylene carbonateHCID 751541,2,3,4-Tetrachloro-5,5-dimethoxycyclopenta-1,3-diene

Produkt 1

HCID 14271043HCID 14271043, VerbindungAusbeute 94,5 %

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a 500 mL 3N RB flask equipped with a water condenser, N2 flow adapter and thermometer, was placed 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopentadiene (20.7 g, 0.078 mol) and vinylene carbonate (6.7 g, 0.078 mol). The mixture was heated to 90° C. for 4 h, then at 60° C. for 63 h. The reaction was judged complete by TLC and upon cooling, the product solidified, was recrystallized from THF and filtered to provide a white solid (25.80 g, 94%). (TLC 20% EtOAc/hexanes Rf 0.29); 1H NMR (400 MHz, CDCl3) δ 5.13 (s, 2H), 3.59 (s, 3H), 3.56 (s, 3H); GCMS m/z 348 (M)+; mp 160–162° C.; Anal. Calcd. for C10H8Cl4O5: C, 34.32; H, 2.30. Found C, 34.32; H, 2.27.

Aufarbeitung

  1. customIn a 500 mL 3N RB flask equipped with a water condenser, N2 flow adapter
  2. temperatureupon cooling
  3. customwas recrystallized from THF
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-4b7d4f1e09594a07a76c3ab10e97afc9
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07241887B2

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