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2-Methoxyethoxymethyl chloride

Chemical compound From Wikipedia, the free encyclopedia

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2-Methoxyethoxymethyl chloride is an organic compound with formula CH3OCH2CH2OCH2Cl. A colorless liquid, it is classified as a chloroalkyl ether. It is used as an alkylating agent. In organic synthesis, it is used for introducing the methoxyethoxy ether (MEM) protecting group.[2] MEM protecting groups are generally preferred to methoxymethyl (MOM) protecting groups, both in terms of formation and removal.

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Typically, the alcohol to be protected is deprotonated with a non-nucleophilic base such as N,N-diisopropylethylamine (DIPEA, Hunig's base) in dichloromethane followed by addition of 2-methoxyethoxymethyl chloride.[3] [4]

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The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.[5]

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Safety

The closely related chloromethyl methyl ether is a known human carcinogen.[6]

References

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