In organic chemistry, a methoxymethyl ether is a functional group with the formula ROCH2OCH3, abbreviated MOM. The group is usually derived from chloromethyl methyl ether, a kind of chloroalkyl ether which is, like its congeners, often employed in organic synthesis to protect alcohols. [1] [2] Closely related to MOM ethers are methoxyethoxymethoxy (MEM) protecting groups, introduced using 2-methoxyethoxymethyl chloride. The MEM protecting groups are more easily installed and more easily removed.
Typically, the alcohol is protected by addition of the chloromethyl reagent [3] followed by deprotonation with a non-nucleophilic base such as N,N-diisopropylethylamine (DIPEA) in dichloromethane.
Although not relevant to protecting groups, MOM groups are installed by reaction of chloromethyl ethers with methoxide [4] and by the acid-catalyzed reaction of alcohols with dimethoxymethane. [5]
The MOM and the MEM protecting groups can be cleaved with a range of Lewis and Bronsted acids. [6]
Chloromethyl methyl ether and chloromethoxyethoxymethane, like other chloroalkyl ethers, are strong alkylating agents with attendant dangers. These compounds are human carcinogen. [7]
{{cite journal}}
: CS1 maint: multiple names: authors list (link){{cite journal}}
: CS1 maint: multiple names: authors list (link)