Print version Print setup

Deprotection of trimethylsilyl group of an alkyne; enynes

SyntheticPage 100
DOI: 10.1039/SP100
Submitted Aug 17, 2001, published Aug 17, 2001
Marco Soscia (m.g.soscia@sussex.ac.uk)
A contribution from Caddick, Sussex


			Reaction Scheme: Deprotection of trimethylsilyl group of an alkyne

Chemicals Used

K2CO3 (aldrich anhydrous)
MeOH (distilled over CaH2)

Procedure

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%)

Author's Comments

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.

Data

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)

Lead Reference

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

This page has been viewed approximately 14977 times since records began.

Get structure file (.cdx, .sk2, .mol)

Keywords: TMS-deprotection, desilylation, 100

Post new comment
Loading ...