Water → HCID 14407228, compound

Participants

Reaction Steps

3-Bromo-2-oxopropylidenetriphenylphosphorane (17.85 g) was added to a solution of thiophenol (5.22 g; 4.86 ml) in anhydrous ethanol (70 ml) containing sodium (1.09 g). The mixture was heated at reflux for 150 minutes and was then poured into a mixture of ice and water (250 ml). The mixture was then extracted with dichloromethane and the extract was washed with dilute aqueous sodium hydroxide solution (2 N) and then with water, and was dried over magnesium sulphate. Evaporation of the solvent gave a residual oil which was triturated with petroleum ether (b.p. 40°-60° C.), and the resulting crude solid was recrystallised from a mixture of toluene and petroleum ether (b.p. 60°-80° C.) to give 2-oxo-3-phenylthiopropylidenetriphenylphosphorane (14.2 g) in the form of cream prisms, m.p. 132°-134° C. [elemental analysis: C, 76.4; H, 5.3; P, 7.3; S, 7.7%. C27H23OPS requires C, 76.0; H, 5.4; P, 7.3; S, 7.5%. νmax 715, 740, 750, 1110, 1385, 1440, 1485 and 1550 cm-1 ].

Provenance & Evidence