K₂CO₃ (aldrich anhydrous)
MeOH (distilled over CaH₂)

To a solution of TMS-alkyne (14.86g, 31.52mmol) in methanol (250ml) was added potassium carbonate (0.54g, 3.9mmol) and the mixture stirred for 2hrs at room temperature under N₂. The reaction mixture was then concentrated in vacuo, and the residue diluted with ether, washed with water, brine and dried over MgSO₄, filtered and concentrated in vacuo. Purification by flash chromatography eluting with 25:1 petrol/ether yielded the title copmound as an orange solid (10.26g, 82%)

This transformation has been carried out numerous times in the lab on various substrates. Although in this example no problems were identified, in other examples serious reductuion in yield was noted when the reaction was left for longer periods.

¹H: 7.58 (m, 4H), 7.35 (m, 6H), 6.45 (s, 1H), 4.25 (s, 2H), 3.23 (s, 1H), 1.00 (s, 9H)

S.Caddick, V.M.Delisser, V.E.Doyle, S.Khan, Tetrahedron, 1999, 2737-2754