Synthesis
To a solution of 4-pentyn-1-ol (5.9 g, 70 mmol, 1.0 eq.) in THF (100 mL) was slowly added n-butyllithium (2.50 M hexane solution, 60.0 mL, 147 mmol, 2.10 eq.) dropwise at -78 °C. The reaction mixture was slowly warmed to room temperature and then cooled again to -78°C. Subsequently, freshly distilled trimethylchlorosilane (20.0 mL, 154 mmol, 2.20 eq.) was added dropwise to the mixture and slowly warmed to room temperature. The reaction was kept stirred for 2 hours. After completion of the reaction, the reaction was quenched with 3M HCl aqueous solution and the resulting biphasic system was stirred vigorously for 3 hours. The aqueous layer was separated, extracted twice with ether (Et2O), the organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4), filtered and concentrated to quantitatively obtain 5-(trimethylsilyl)-4-pentyn-1-ol.
References
[1] Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 739 - 743
[2] Angew. Chem., 2013, vol. 125, # 2, p. 767 - 771,5
[3] Arkivoc, 2014, vol. 2014, # 3, p. 287 - 296
[4] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2051 - 2060
[5] Chemistry - A European Journal, 2013, vol. 19, # 38, p. 12649 - 12652
