Water → HCID 20399562, compound

Participants

Reaction Steps

A solution of 6.6 ml (0.06 M) of TiCl4 in 15 ml of CCl4 was added dropwise to 120 ml of ice-cooled dry THF (120 ml) under argon. The resulting bright yellow suspension was added quickly to a solution of 8.9 gm (0.03 M) of 2,6-diphenyl-4H-thiopyran-4-one-1,1-dioxide and 3.4 gm (0.03 M) of ethyl cyanoacetate in 70 ml of THF. The mixture was stirred for 20 minutes in the ice-bath. Then 9.5 gm (0.12 M) of dry pyridine was then added. After stirring at room temperature overnight 30 ml of H2O and a small amount of ether was added to the reaction mixture. The organic phase was separated, washed with dilute NaHCO3, brine, dried (MgSO4) and rotavaporated to give 11.4 gm of a highly fluorescent yellow solid. The latter solid was recrystallized from toluene containing a little hexane to give the titled compound (mp 156°-7° C.).

Provenance & Evidence