Triphenylphosphine → 3-{1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethoxy}-cyclopent-2-enone

Participants

Reaction Steps

To a solution of 1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethanol (4.1 g, 17.1 mmol) in anhydrous THF (100 ml), at 0° C. under an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.18 g, 22.23 mmol), followed by triphenylphosphine (5.83 g, 22.23 mmol). Diisopropylazodicarboxylate (4.31 ml, 22.23 mmol) was then added dropwise over a period of 5 minutes and the reaction allowed to warm to room temperature and stirred for 2 hours. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 3-{1-[2-(4-Chloro-phenyl)-thiazol-5-yl]-ethoxy}-cyclopent-2-enone (2.29 g).

Provenance & Evidence