Diethyl Ether → 4-Trimethylsilyl-3-butyn-1-ol

Participants

Reaction Steps

A solution of 33.25 parts of 3-butyn-1-ol in 500 parts by volume ether is cooled to -60° C. under argon and treated dropwise with 400 parts by volume of a 2.5 molar solution of n-butyl lithium in hexane. One hour after the addition is complete, a solution of 130 parts by volume of trimethylchlorosilane in 130 parts by volume of ether is added dropwise. After the addition is complete, the temperature is allowed to rise to 0°. The reaction mixture is poured into water, washed with 1NHCl 3 times, additional water, dried over sodium sulfate and evaporated to a liquid which is distilled under water aspirator pressure to give 4-trimethylsilyl-3-butyn-1-ol, bp. 75-77 (13 Tor).

Provenance & Evidence