Is it possible to use CI3TMS (a carbon with three iodo groups and a trimethylsilyl protecting group) and three equivalents of an ethyl grignard reagent to prepare 3-ethylpentan-3-ol? By deprotecting the product after the grignard reaction using tributylammonium fluoride, is it possible to produce the desired product? I have studied a more lengthy method of arriving at the product; however, I cannot find any reference to my proposed mechanism, which seems shorter and more efficient. Is there some sort of flaw in my mechanism, or would it theoretically work?

CI3TMS --- 1) BrMgEt, diethyl ether 2) TBAF ---> 3-ethylpentan-3-ol

  • $\begingroup$ I think you're missing an oxygen, when an alcohol is protected by TMSCl, it becomes a TMS ether, thus the reagent you need is I3COTMS. $\endgroup$ – szentsas Aug 13 '19 at 19:15
  • 2
    $\begingroup$ Did you mean 3-ethylpentan-3-ol? Much easier with 2 equivalents of ethyl magnesium bromide and methyl or ethyl propionate if a different method is appropriate. $\endgroup$ – user55119 Aug 13 '19 at 19:23
  • $\begingroup$ I'm pretty sure he did $\endgroup$ – szentsas Aug 13 '19 at 19:42

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