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Decent references for SN2 displacement of tosylate with acetylide

  1. Jun 22, 2012 #1
    i'm having trouble finding good references for lithiating a terminal alkyne and reacting that acetylide with a tosylate, and my goto procedure didn't work. can anyone give me a hand?

    procedure i did try:

    alkyne in THF at -78
    1.0 eq nBuLi added
    1.0 eq tosylated phenylethanol added (color change here) still at -78
    ammonium chloride workup

    despite the color change, the NMR and TLC just show a mixture of starting materials and i'm a bit baffled as to why our normal run-through didn't succeed. maybe adding ethylenediamine or TMEDA is necessary?
  2. jcsd
  3. Jun 22, 2012 #2
    meh, pretty sure i fixed it by adding 20% v/v DMSO and warming after adding the tosylate.
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