Water → Isohexane ethyl acetate

Participants

Reaction Steps

To a solution of 16.3 g (44.0 mmol) C2 in 260 ml dry THF at 10° C. under nitrogen 1.5 g (2.2 mmol) bis-(triphenylphosphine)palladium-II-chloride, 900 mg (4.7 mmol) copper-I-iodide, 12 ml (85 mmol) trimethylsilylacetylene and 30 ml diisopropylamine were added and the mixture was stirred and successively allowed to warm up to room temperature. After stirring at room temperature overnight, 260 ml water were added and the mixture was extracted twice with ether. The organic layer was separated, dried and evaporated to dryness. Column chromatography of the residue on SiGel (iso-hexane/ethyl acetate 3:1) yielded 12.5 g (83%) C17.

Provenance & Evidence