Trimethylsilylacetylene → HCID 101337817, compound

Participants

Reaction Conditions

Reaction Steps

A flame-dried 250-mL round-bottom flask was cooled under nitrogen and placed in an ice bath. Into this flask was added 30 mL pentane and 3.6 g (36 mmol) trimethylsilylacetylene. n-Butyllithium (13.2, 2.5 M in hexane) was added over 12 minutes, and the reaction was allowed to stir for one hour at 0° C. Diisopropylchlorosilane (5.1 g, 34 mmol) was then added, and the reaction stirred overnight. The solution was extracted with pentane (2×40 mL) and the organic layers were washed with water, dried over magnesium sulfate, filtered, then carefully concentrated using rotary evaporation (product was volatile). Chromatography on silica with pentane as an eluent yielded 6.9 g (33 mmol, 99%) the desired product as a clear oil.

Provenance & Evidence