Boron trifluoride → (R)-1-((tert-Butyldimethylsilyl)oxy)-5-(trimethylsilyl)pent-4-yn-2-ol

Participants

Reaction Conditions

Reaction Steps

tert-BuLi (12.4 ml, 1.7M, 21.1 mmol) was added to a solution of TMS-acetylene (2.12 g, 21.7 mmol) in THF (40 ml) at −78° C. and the reaction mixture was stirred for an additional 30 min. (R)-tert-butyldimethyl(oxiran-2-ylmethoxy)silane (2 g, 10.6 mmol) and BF3.EtO2 (3 g, 21.1 mmol) were added and stirred at −78° C. for 4.5 hours. The reaction was then quenched by addition of aqueous ammonium chloride solution and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford the desired material in a quantitative yield. The material was used in the next step with no further purification.

Provenance & Evidence