Dimethyl Sulfoxide → (Z)-7-phenyl-7-pyridin-3-ylhept-6-enoic acid

참여 물질

반응 조건

반응 단계

To dimethylsulfoxide (40 ml) was added dropwise sodium hydride (1.0 g), and the mixture was heated at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, to which was added 5-carboxypentyltriphenyl phosphonium bromide (9.5 g, 21 mmoles) and the mixture was stirred for 5 minutes. To the reaction mixture was added a tetrahydrofuran solution (10 ml) of 3.7 g (0.02 mole) of 3-benzoylpyridine. The mixture was stirred for 30 minutes at room temperature, followed by addition of water (100 ml), which was subjected to extraction twice with ethylacetate (50 ml). The aqueous layers were combined and adjusted to pH 6 with 2N HCl, which was subjected to extraction with ethyl acetate. The organic layers were combined and washed with water and dried (magnesium sulfate). The solvent was then evaporated off, and the residue was subjected to silica-gel chromatography, using ethanolethyl acetate (1:5) as eluant to yield (E)+(Z)-7-(3-pyridyl)-7-phenyl-6-heptenoic acid (Ia-3, Ia-4 in Table 3) (4.5 g 79%).

출처 및 근거