Triisopropylsilyl trifluoromethanesulfonate → 1-(Triisopropylsilyl)-1-propyne

Participants

Reaction Steps

1-Propynyllithium (7.18 g, 156 mmol) was stirred in 160 mL of anhydrous ether at -40° C. under nitrogen and treated dropwise with triisopropylsilyl trifluoromethanesulfonate (47.8 g, 41.93 mL, 156 mmol). The reaction was warmed to room temperature, washed with 2×100 mL of water and 1×100 mL of brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Flash chromatography (95 mm column, petroleum ether eluent, 51/2 inches of silica gel) afforded 25.7 g (84%) of product as a colorless oil.

Provenance & Evidence