Methoxymethylenetriphenylphosphine is a

Wittig reagent In organic chemistry, Wittig reagents are organophosphorus compounds of the formula R3P=CHR', where R is usually phenyl. They are used to convert ketones and aldehydes to alkenes: : Preparation Because they typically hydrolyze and oxidize readily ...

used for the

homologization In organic chemistry, a homologation reaction, also known as homologization, is any chemical reaction that converts the reactant into the next member of the homologous series. A homologous series is a group of compounds that differ by a constant u ...

of aldehydes, and

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

s to extended aldehydes, a

organic reaction Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organ ...

first reported in 1958. The

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

is generally prepared and used in situ. It has blood-red color, indicative of destabilized

ylide An ylide or ylid () is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms h ...

Preparation

The reagent can be prepared in two steps from triphenylphosphine. The first step is ''P''- alkylation with

chloromethyl methyl ether Chloromethyl methyl ether (CMME) is a compound with formula CH3OCH2Cl. A colorless liquid, it is a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting ...

. : In the second step, the resulting phosphonium salt is deprotonated. : In place of chloromethyl methyl ether, a mixture of

methylal Dimethoxymethane, also called methylal, is a colorless flammable liquid with a low boiling point, low viscosity and excellent dissolving power. It has a chloroform-like odor and a pungent taste. It is the dimethyl acetal of formaldehyde. Dimetho ...

and acetyl chloride can be used.

Uses

This reagent reacts with a ketone or aldehyde in a Wittig reaction to give an

enol ether In organic chemistry an enol ether is an alkene with an alkoxy substituent. The general structure is R2C=CR-OR where R = H, alkyl or aryl. A common subfamily of enol ethers are vinyl ethers, with the formula ROCH=CH2. Important enol ethers include ...

, which can be converted to the aldehyde by acid-induced hydrolysis. The initial report of the reaction demonstrated its use on the

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and a ...

tigogenone. : It was later used in the

Wender Taxol total synthesis Wender Taxol total synthesis in organic chemistry describes a Taxol total synthesis (one of six to date) by the group of Paul Wender at Stanford University published in 1997.''The Pinene Path to Taxanes. 6. A Concise Stereocontrolled Synthesis o ...

and the

Stork quinine total synthesis The total synthesis of quinine, a naturally-occurring antimalarial drug, was developed over a 150-year period. The development of synthetic quinine is considered a milestone in organic chemistry although it has never been produced industrially as ...

References

# {{Note, Levine ''A new aldehyde synthesis'' Samuel G. Levine

J. Am. Chem. Soc. The ''Journal of the American Chemical Society'' is a weekly peer-reviewed scientific journal that was established in 1879 by the American Chemical Society. The journal has absorbed two other publications in its history, the ''Journal of Analytic ...

; 1958; 80(22); 6150–6151. doi:10.1021/ja01555a068 Homologation reactions Organophosphanes