Jackson
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Chloroform in ether synth?
Could chloroform be used in a Williamson ether synthesis? Would a reaction with sodium ethoxide produce something like tri ethoxymethane or would it
stop reacting after the first or second ethoxy group was added?
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DavidJR
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Yes, this is one way to produce triethoxymethane, also known as triethyl orthoformate.
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fusso
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Nurdrage made (MeO)3CH in this vid. I believe Et version can be made this way too.
https://www.youtube.com/watch?v=TmUNTkP2nw0
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Jackson
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Could lithium metal be used in substitution for sodium metal? Just because lithium can be obtained from batteries and it's something that I have
access to because of that. I could have access to sodium, but I already have lithium so if it can be used that would be preferable.
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fusso
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I think so, the alkali ion is only a counterion and changing it have little effect on nucleophilic substitution.
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Sigmatropic
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Agree with fusso, Except that the oxygen lithium bond is stronger than sodium oxygen. In my experience*, lithium alkoxide are less potent nucleophiles
than sodium alkoxides. Generally requiring additives or polar aprotic solvents to work, if I recall the short literature search I did at the time.
*in the comparison between the two step procedure of an organolithium with a benzophenone in THF, acidic work-up to the alcohol then NaH/DMF, alkyl
tosylate to give an ether and the single pot procedure of organolithium, benzophenone, then alkyl tosylate all in THF, which after isolation gave the
alcohol as the primary product.
Could've been the solvent during alkylation, could've been the difference between sodium and lithium.
[Edited on 12-2-2019 by Sigmatropic]
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