Vinylene carbonate → HCID 14271043, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence