Acetic Acid → Dimethyl(2-oxo-4-phenylbutyl)phosphonate

Participants

Reaction Steps

To a solution of dimethyl methylphosphonate (115.5 g.) in tetrahydrofuran (2.1 l.) at -65°, there is added 660 ml. of a 1.6 M solution of n-butyl lithium in hexane, and then there is added a solution of ethylhydrocinnamate (93.5 g.) in tetrahydrofuran (225 ml.). The mixture is stirred at -65° for 2 hrs. and then stirring is continued at 25° for 16 hrs. Acetic acid (70 ml.) is added, the solution is concentrated under reduced pressure and the residue is partitioned between methylene chloride and water. The organic layer is dried, concentrated, and distilled at 2 mm. to give 121.5 g. of the title compound; b.p. 184-195; mass spectrum 256 (M+).

Provenance & Evidence