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

温度

80 °C

Sodium hydride (2.5 g, 60% oil dispersion) was washed with hexane, to make clean of the oil and dried under reduced pressure. Dimethylsulfoxide (25 ml) was added to it, and the mixture was heated under argon at 80° C. for 1 hour to produce dimsyl anions. The reaction solution was cooled at 10° C., and 5-carboxy-5,5-dimethylpentyltriphenylphosphonium bromide (8 g, 16 mmole) was added, followed by stirring at room temperature for another 10 minutes. A dimethylsulfoxide solution (5 ml) containing 3-benzoylpyridine (3 g, 16 mmole) was added dropwise to the mixture solution, and after the completion of the dropwise addition, stirring was continued at room temperature for 30 minutes. Water (50 ml) was added to the mixture, which was then shaken. The organic layer was separated, and the water layer was adjusted to pH 6.0 with 2N hydrochloric acid. The product was extracted three times with ethyl acetate (50 ml). The ethyl acetate layers were combined, washed with water, dried (over magnesium sulfate) 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) (2.2. g).

1. washSodium hydride (2.5 g, 60% oil dispersion) was washed with hexane
2. customdried under reduced pressure
3. additionDimethylsulfoxide (25 ml) was added to it
4. customto produce dimsyl anions
5. temperatureThe reaction solution was cooled at 10° C.
6. additionwas added dropwise to the mixture solution
7. additionafter the completion of the dropwise addition
8. stirringstirring
9. waitwas continued at room temperature for 30 minutes
10. stirringwas then shaken
11. customThe organic layer was separated
12. extractionThe product was extracted three times with ethyl acetate (50 ml)
13. washwashed with water
14. dry with materialdried (over magnesium sulfate)
15. concentrationconcentrated under reduced pressure
16. customThe residue was chromatographed on a column of silica gel, and development

ORDレコード

ord-efe384ee8d3d40dfab3a55a34b250b96

出典データセット

uspto-grants-1985_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04518602