Water → 1,3-Di-tert-butyl-5-ethynylbenzene

Participants

Reaction Conditions

Reaction Steps

73.7 g (0.655 mol) of potassium tert-butanolate were added a little at a time to 117.6 g (0.269 mol) of bromomethyltriphenylphosphonium bromide in 420 ml of dry tetrahydrofuran at 25° C. while cooling. The reaction mixture was then stirred for half an hour and, at -70° C., a solution of 50 g (0.218 mol) of 3,5-di-tertbutylbenzaldehyde in 120 ml of dry tetrahydrofuran was added dropwise. After half an hour, the mixture was allowed to warm to room temperature, and was then stirred overnight and poured into water. Extraction with ether, washing of the organic phase with water, drying over sodium sulfate and evaporation of the solvent produced a viscous residue.

Provenance & Evidence