1-(Triphenylphosphoranylidene)acetone → [1-(3-Oxobut-1-en-1-yl)cyclopropyl]acetonitrile

Participants

Reaction Steps

A mixture of the aldehyde from Example 1, Step 2 (8.12 g, 75 mmol) and 1-triphenylphosphoranylidene-2-propanone (26.4 g, 83 mmol) in 250 mL THF was heated to reflux overnight. The reaction mixture was partitioned between 1N HCl and ethyl acetate, and the organic layer was washed with brine, dried over MgSO4 and evaporated. Et2O was added to the residue, the phosphine oxide was filtered off and the solvent removed in vacuo. Purification through a plug of silica gel provided 10.3 g of the title compound.

Provenance & Evidence