Methyl (triphenylphosphoranylidene)acetate

Chemical properties

white to off-white powder

The Uses of Methyl (triphenylphosphoranylidene)acetate

1. (Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates.
2. used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.
3. It is used in the preparation of (triphenylphosphoranylidene)-ketene.
4. The Wittig reaction we performed in class involved the reaction of 2-nitrobenzaldehyde (1) with methyl (triphenylphosphoranylidene) acetate (2) to produce methyl (2E)-3-(2-nitrophenyl) acrylate (3) with a triphenylphosphine oxide (4) side product, and took place in a silica gel matrix to ensure even product dispersion for chromatography.
   

The Uses of Methyl (triphenylphosphoranylidene)acetate

(Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Further, it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates. It is used in the preparation of (triphenylphosphoranylidene)-ketene.

The Uses of Methyl (triphenylphosphoranylidene)acetate

Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. Also used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.

Purification Methods

Crystallise it by dissolving in it AcOH and adding pet ether (b 40-50o) to give colourless plates. UV max (A 1mm ): 222nm (865) and 268nm (116) [Isler et al. Helv Chim Acta 40 1242 1957]. [Beilstein 16 IV 977.]