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(Ethoxycarbonylmethylene)triphenylphosphoran is used as a Wittig reagent in organic synthesis. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone. It acts as an inhibitor and inhibits the activity of cholinesterase.
Stable crystalline ylide which reacts with aldehydes giving substituted ethyl acrylates. This reaction has been used in an indole synthesis from o-nitrobenzaldehydes: Synthesis, 862 (1984); 401 (1987):
Coumarins have been synthesized from o-hydroxy acetophenones: Monatsh. Chem., 115, 765 (1984); o-hydroxy aldehydes give the 4-unsubstituted analogues: Chem. Pharm. Bull., 39, 3100 (1991); 42, 2032 (1994); Indian J. Chem. B, 32, 1159 (1993):
More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).
Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).
See also (Methoxycarbonylmethylene)triphenylphosphorane, A14020, and Appendix 1./n
Bujaranipalli, S.; Das, S. Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: a facile and stereoselective approach. Tetrahedron Lett. 2015, 56 (24), 3747-3749.
Nagaraju, K.; Mainkar, P. S.; Chandrasekhar, S. Convergent synthesis of fully functionalized decalin skeleton of (+)-fusarisetin A. Tetrahedron Lett. 2015, 56 (2), 404-405.