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Chloromethyl methyl ether (CMME) is a compound with formula CH 3 OCH 2 Cl. A colorless liquid, it is a chloroalkyl ether.It is used as an alkylating agent.In organic synthesis, it is used for introducing the methoxymethyl ether (MOM) protecting group, [3] and is thus often called MOM-Cl or MOM chloride.
Chemical structure of chloromethyl methyl ether (MOM-Cl) Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH 2) n-Cl, characterized as an ether connected to a chloromethyl group via an alkane chain. Chloromethyl methyl ether (CMME) is an ether with the formula C H 3 OCH 2 Cl.
The first step is P-alkylation with chloromethyl methyl ether. PPh 3 + CH 3 OCH 2 Cl → [CH 3 OCH 2 PPh 3]Cl. In the second step, the resulting phosphonium salt is deprotonated. [CH 3 OCH 2 PPh 3]Cl + LiNR 2 → CH 3 OCH=PPh 3 + LiCl + HNR 2. In place of chloromethyl methyl ether, a mixture of methylal and acetyl chloride can be used.
It is a kind of chloroalkyl ether and, like its congeners, often employed in organic synthesis to protect alcohols. They are usually derived from 2-methoxymethyl chloride. [1] [2] Closely related to MOM ethers are methoxyethoxymethoxy (MEM) protecting groups, introduced using 2-methoxyethoxymethyl chloride. The MEM protecting groups are more ...
For example, diagrammed below is an excerpt of the synthesis of an analogue of Mitomycin C by Danishefsky. [110] Part of the synthesis of an analogue of Mitomycin C with modified reactivity through protecting-group exchange. The exchange of a protecting group from a methyl ether to a MOM-ether inhibits here the opening of an epoxide to an aldehyde.
2-Methoxyethoxymethyl chloride is an organic compound with formula CH 3 OCH 2 CH 2 OCH 2 Cl. 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]
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The chain mechanism is as follows, using the chlorination of methane as an example: Initiation Ultraviolet radiation splits a chlorine molecule to two chlorine atom radicals. Methane chlorination: initiation Chain propagation (two steps) A radical abstracts a hydrogen atom from methane, leaving a primary methyl radical.