Tetrabutylammonium Fluoride → 2-Ethynyl-1,3-dimethylbenzene

Participants

Reaction Steps

To an ice cold solution of (2,6-dimethylphenylethynyl)-trimethylsilane from the previous step in THF (20 mL) was added tetrabutylammonium fluoride in THF (17 mL of 1 M solution) dropwise. After stirring 18 h, the solution was diluted with hexane and extracted with water and brine. The organic layer was dried, filtered, and solvent removed under reduced pressure. The residual oil was redissolved in hexane and filtered through a silica gel plug, then chromatographed using hexane as eluent to give 2,6-dimethylphenylacetylene.

Provenance & Evidence