Water → 2,2-Dimethyl-7-phenyl-7-pyridin-3-yl-hept-6-enoic acid

Beteiligte Stoffe

Reaktionsschritte

5-Carboxy-5,5-dimethylpentyltriphenylphosphonium bromide (3 g, 6 mmole) was dissolved in anhydrous dimethylsulfoxide (30 ml) under a nitrogen atmosphere, and sodium hydride (0.25 g, 64 mmole) was added to the solution at 30° to 35° C., followed by stirring at 25° to 30° C. for 30 minutes. 3-Benzoylpyridine (0.9 g, 5 mmole) was added to the solution, followed by stirring at room temperature for another 1 hour. Water (100 ml) and toluene (100 ml) were added to the reaction solution, the organic layer was separated, and the water layer was adjusted to pH 6.0 with 2N hydrochloric acid. The product was extracted with ethyl acetate, and the ethyl acetate layer was washed with water, dried and concentrated under reduced pressure. The residue was chromatographed on a column of silica gel, and development was effected with ethyl acetate to yield (E+Z)-2,2-dimethyl-7-phenyl-7-(3-pyridyl)-6-heptenoic acid (2-a, 2-b) (1.36 g, 88%).

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