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Methoxymethylenetriphenylphosphine



Methoxymethylenetriphenylphosphine is a Wittig reagent with used as an reagent in the homologization of aldehydes and ketones to extended aldehydes, an organic reaction first reported in 1958 [1].

Additional recommended knowledge

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


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.

References

  1. ^  A new aldehyde synthesis Samuel G. Levine J. Am. Chem. Soc.; 1958; 80(22); 6150-6151. Abstract
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Methoxymethylenetriphenylphosphine". A list of authors is available in Wikipedia.
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