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Methoxymethyl ether

Functional part of an organic molecule

Methoxymethyl ether
Summary

Functional part of an organic molecule

In organic chemistry, a methoxymethyl ether is a functional group with the formula , 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. 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 is protected by addition of the chloromethyl reagent 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 and by the acid-catalyzed reaction of alcohols with dimethoxymethane.

Deprotection

The MOM and the MEM protecting groups can be cleaved with a range of Lewis and Brønsted acids.

Safety

Chloromethyl methyl ether and chloromethoxyethoxymethane, like other chloroalkyl ethers, are strong alkylating agents with attendant dangers. These compounds are human carcinogen.

References

References

  1. (2006). "Greene's Protective Groups in Organic Synthesis". J. Wiley.
  2. (2000-04-17). "Diastereo- and Enantioselective Total Synthesis of Stigmatellin A". Chemistry – A European Journal.
  3. (2019). "Preparation of (R)-3-(3,5-Bistrifluoromethylphenyl)-1,1'-bi-2-naphthol". Organic Syntheses.
  4. William F. Bailey, Matthew W. Carson, Lyn M. J. Zarcone. (1998). "Selective Protection of 1,3-Diols at the More Hindered Hydroxy Group: 3-(Methoxymethoxy)-1-Butanol". Organic Syntheses.
  5. Kohei Tamao, Yoshiki Nakagawa, and Yoshihiko Ito. (1996). "Regio- AND Stereoselective Intramolecular Hydrosilylation of a-Hydroxy Enol Ethers: 2,3-syn-2-Methoxymethoxy-1,3-nonanediol". Organic Syntheses.
  6. (1999-03-26). "Total synthesis of paniculide A from d-glucose". Tetrahedron.
  7. [https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/bis_chloromethyletherandtechnical-gradechloromethylmethylether.pdf 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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