Everything about Methoxymethylenetriphenylphosphine totally explained
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 .
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.
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.
Further Information
Get more info on 'Methoxymethylenetriphenylphosphine'.
|
External Link Exchanges
Do you know how hard it is to get a link from a large encyclopaedia? Well we're different and will prove it. To get a link from us just add the following HTML to your site on a relevant page:
<a href="http://methoxymethylenetriphenylphosphine.totallyexplained.com">Methoxymethylenetriphenylphosphine Totally Explained</a>
Then simply click through this link from your web page. Our crawlers will verify your link, extract the title of your web page and instantly add a link back to it. If you like you can remove the words Totally Explained and embed the link in article text.
As long as your link remains in place, we'll keep our link to you right here. Please play fair - our crawlers are watching. Your site must be closely related to this one's topic. Any kind of spamming, dubious practises or removing the link will result in your link from us being dropped and, potentially, your whole site being banned. |
