Английская Википедия:2-Methoxyethoxymethyl chloride

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Шаблон:Chembox

2-Methoxyethoxymethyl chloride is an organic compound with formula Шаблон:Chem2. 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.[1] MEM protecting groups are generally preferred to methoxymethyl (MOM) protecting groups, both in terms of formation and removal.

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 2-methoxyethoxymethyl chloride.[2] [3]

Файл:MOMDepr.png

The MEM protecting group can be cleaved (deprotection) with a range of Lewis and Bronsted acids.[4]

Safety

The closely related chloromethyl methyl ether is a known human carcinogen.[5]

References

  1. Шаблон:Cite book
  2. Шаблон:Cite journal
  3. Шаблон:Cite journal
  4. Шаблон:Cite journal
  5. bis(Chloromethyl) Ether and Technical-Grade Chloromethyl Methyl Ether CAS Nos. 542-88-1 and 107-30-2 Report on carcinogens, eleventh edition