Triphenylphosphine → 3-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enone

Participants

Reaction Steps

To a solution of [2-(4-Chloro-phenyl)-thiazol-5-yl]-methanol (4.89 g, 21.75 mmol) in anhydrous THF (100 ml), at 0° C. under an atmosphere of nitrogen was added cyclopentane-1,3-dione (2.78 g, 28.27 mmol) followed by triphenylphosphine (7.41 g, 28.27 mmol). Diisopropylazodicarboxylate (5.48 ml, 28.27 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-[5-(4-Chloro-phenyl)-thiophen-2-ylmethoxy]-cyclopent-2-enone (5.1 g).

Provenance & Evidence