3-Butyn-1-OL → [4-(Triethylsilyl)-3-butyn-1-yloxy]triethylsilane

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Reaction Steps

3-butin-1-ol (34.99 g, 0.50 mole) was dissolved in THF (1.2 l) under nitrogen and cooled to −30° C. n-BuLi (640 ml, 1.02 mole, 1.6 M solution in n-hexane) was added dropwise to this solution within 15 minutes at such a rate that the temperature did not exceed −20° C. After 1 hour at −20° C. a solution of triethylchlorosilane (171.4 ml, 1.02 mole) in THF (300 ml) was added dropwise within 30 minutes. The cooling bath was removed and the reaction solution was stirred for 15 hours at RT. The reaction mixture was quenched with aqueous Na2CO3 solution (1%) while cooling in an ice bath and was extracted with hexane (2×500 ml). The combined organic phases were washed with saturated NaCl-Solution (300 ml) and dried over MgSO4. After filtering off the drying agent the solvents were removed on a rotary evaporator and the residue was purified by distillation (p=0.05 mbar, head temperature=115°-110° C.), triethyl(4-(triethylsilyl)but-3-inyloxy)silane (88.9 g, 60%) being obtained.

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