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

Temperature

80 °C

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%).

1. temperatureThe reaction mixture was cooled to room temperature, to which
2. stirringThe mixture was stirred for 30 minutes at room temperature
3. extractionwas subjected to extraction twice with ethylacetate (50 ml)
4. extractionwas subjected to extraction with ethyl acetate
5. washwashed with water
6. dry with materialdried (magnesium sulfate)
7. customThe solvent was then evaporated off

ORD record

ord-4dcca75acd3843ae9e867d6f1684e2bb

Source dataset

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04727078