Methoxymethyl ether
In organic chemistry, a methoxymethyl ether is a functional group with the formula Template:Chem2, 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.
Protection
Typically, the alcohol to be protected is deprotonated with a non-nucleophilic base such as N,N-diisopropylethylamine (DIPEA) in dichloromethane followed by addition of the chloromethyl reagent.[3]<
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]
Deprotection
The MOM and the MEM protecting groups can be cleaved with a range of Lewis and Bronsted acids.[6]
Safety
Chloromethyl methyl ether and chloromethoxyethoxymethane, like other chloroalkyl ethers, are strong alkylating agents with attendant dangers. These compounds are human carcinogen.[7]
References
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- ↑ Bis(chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2, Report on carcinogens, Eleventh edition
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