Hydrochloric Acid → 4-(Triethylsilyl)-3-butyn-1-ol

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Reaction Steps

Triethyl(4-(triethylsilyl)but-3-inyloxy)silane (32.99 g, 110.66 mmole) was dissolved in MeOH (336 ml), 2N HCl (62 ml) was added, and the mixture was stirred for 4 hours at RT. Hexane (250 ml) and H2O (200 ml) were then added to the solution and the aqueous phase was extracted with hexane (3×100 ml). The combined organic phases were washed with H2O (100 ml) and then with saturated NaCl-Solution (50 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator. Column chromatography of the residue (hexane/ether=4:1, then ether) yielded 4-(triethylsilyl)but-3-in-1-ol (19.6 g, 96%) as a colourless oil.

Provenance & Evidence