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Title: Methoxymethylenetriphenylphosphine  
Author: World Heritage Encyclopedia
Language: English
Subject: Wender Taxol total synthesis, Aldehyde, Quinine total synthesis, Chemical infobox/WP:chemistry and Template:Chembox articles
Publisher: World Heritage Encyclopedia


Methoxymethylenetriphenylphosphine is a organic reaction first reported in 1958 . This reagent is quite unstable to even mild temperatures and water. As such it must be made in situ, taking on a blood red color, indicative of destabalized ylides.


The reagent can be prepared (scheme 1) by reaction of triphenylphosphine 1 with chloromethyl methyl ether 2 in diethyl ether to the phosphonium salt 3. 3 can also be prepared from triphenylphosphine, methylal and acetyl chloride, a reaction avoiding the costly and carcinogenic chloroalkyl ether and especially useful for large batches.

This salt is deprotonated to the phosphonium ylide Methoxymethylenetriphenylphosphine 4 by phenyllithium.

Scheme 1. Methoxymethylenetriphenylphosphine reagent in aldehyde homologation


This reagent reacts with a ketone or aldehyde 5 in a Wittig reaction to the enol ether 6, which can be converted to the aldehyde 7 by the application of an acid.

The reaction has been applied to the steroid tigogenone (scheme 2) and in the Wender Taxol total synthesis and in the Stork quinine total synthesis.

Scheme 2. Titogenone homologation


  1. ^ A new aldehyde synthesis Samuel G. Levine J. Am. Chem. Soc.; 1958; 80(22); 6150-6151. Abstract
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