1-(Triphenylphosphoranylidene)acetone → HCID 53798873, compound

Participants

Reaction Steps

A mixture of 29.9 g (0.122 mol) of 6-(4-(methylthio)phenoxy)picolinaldehyde and 42.7 g (0.134 mol) of triphenylphosphoranylidene-2-propanone in 750 mL of benzene was heated at reflux for 2.75 hours and cooled. The solvent was removed in vacuo leaving 77 g of an oily solid which was dissolved in methylene chloride and placed on a column of dry silica gel. The column was eluted with methylene chloride and the fractions containing the desired product were combined. The solvent was removed in vacuo leaving 32.5 g (93.7 percent of theoretical) of an oily product which slowly crystallized upon standing. The above named product melted at 71°-72.5° C.; Rf -0.53, (silica gel, 50:50 ethyl acetate-hexane), 1H NMR (CDCl3) 82.25 (s, 3H, CH3C(O)--), 2.4 (s, 3H, CH3S--) 6.7-7.75 (m, 9H, ArH and --CH=CH--).

Provenance & Evidence