N,N,N',N'-Tetramethylazodicarboxamide → 2-Methyl-2-{2-methyl-4-[5-(3-trifluoromethoxy-phenyl)-pent-4-ynyloxy]-phenoxy}-propionic acid ethyl ester

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Reaction Steps

To an ice cold solution of 50 mg (0.21 mmol) 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590), 48 mg (0.21 mmol) 5-(3-trifluoromethoxy-phenyl)-pent-4-yn-1-ol (example 3C]) and 70 μl (0.25 mmol) tributylphosphine (50 19 μmol) in 5 ml tetrahydrofuran were added 43 mg (0.25 mmol) N,N,N′,N′-tetramethyl azodicarboxamide. The cooling bath was removed and stirring continued for 14 h. The mixture was filtered over celite and the solvent removed under reduced pressure to give a yellow oil which was purified by column chromatography (silica gel, heptane/AcOEt) to obtain 34 mg (80 μmol, 36%) of the title compound as colorless oil.

Provenance & Evidence