Decent references for SN2 displacement of tosylate with acetylide

Join the discussion
Registration is free. Start your own thread to ask a follow-up.
1 reply · 2K views
burningbend
Messages
31
Reaction score
0
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?
 
Chemistry news on Phys.org
meh, pretty sure i fixed it by adding 20% v/v DMSO and warming after adding the tosylate.