反应详情

温度

-78 °C

tert-Butyl lithium (2 eq) is added to a solution of TMS-acetylene (2 eq) in THF at −78° C. and the reaction mixture stirred for an additional 30 min. (S)-tert-butyldimethyl(oxiran-2-ylmethoxy)silane (1 eq) and BF3.EtO2 (2 eq) are added and stirred at −78° C. for 4.5 hours. The reaction is quenched by addition of aqueous ammonium chloride solution and extracted with ethyl acetate (3×). The combined organic layers are washed with brine, dried (MgSO4) and concentrated under reduced pressure to afford (S)-1-(tert-butyldimethylsilyloxy)-5-(trimethylsilyl)pent-4-yn-2-ol.

1. additionEtO2 (2 eq) are added
2. customThe reaction is quenched by addition of aqueous ammonium chloride solution
3. extractionextracted with ethyl acetate (3×)
4. washThe combined organic layers are washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under reduced pressure