Decent references for SN2 displacement of tosylate with acetylide

  • #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?
 

Answers and Replies

  • #2
meh, pretty sure i fixed it by adding 20% v/v DMSO and warming after adding the tosylate.
 

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