Dimethyl Sulfoxide → HCID 13285834, Verbindung

Temperatur

85 °C

Sodium hydride (60% in oil, 10 g, 0.25 mole) was added to dimethyl sulfoxide (250 ml) under argon and the mixture was stirred at 85° C. for an hour. The mixture was then cooled to room temperature and 5-carboxypentyltriphenylphosphonium bromide (52 g, 0.11 mole) was added gradually with the temperature being maintained at 40° C. The resulting mixture was stirred for 10 minutes, and a solution of 2-nicotinoylthiophene (20 g, 0.11 mole) in tetrahydrofuran (60 ml) was added dropwise. After the addition, the mixture was stirred at room temperature for 30 minutes, and water (300 ml) was added. The aqueous solution was extracted twice with toluene (300 ml) to remove the neutral substance. The aqueous layer was adjusted to pH 5.5 with 2N hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography using ethyl acetate as eluant and the eluate was concentrated. The resulting oily product was dissolved in ethyl acetate and the solution was allowed to stand overnight to give (Z)-7-(3-pyridyl)-7-(2-thienyl)-6-heptenoic acid (9 g, 29%). Mp 93°-94° C.

1. temperatureThe mixture was then cooled to room temperature
2. temperaturebeing maintained at 40° C
3. stirringThe resulting mixture was stirred for 10 minutes
4. additionAfter the addition
5. stirringthe mixture was stirred at room temperature for 30 minutes
6. extractionThe aqueous solution was extracted twice with toluene (300 ml)
7. customto remove the neutral substance
8. extractionextracted with ethyl acetate
9. washThe ethyl acetate layer was washed with water
10. dry with materialdried (magnesium sulfate)
11. concentrationconcentrated under reduced pressure
12. concentrationthe eluate was concentrated
13. dissolutionThe resulting oily product was dissolved in ethyl acetate

ORD-Eintrag

ord-06b4a9fc73af486aaef1030ea95c72c8

Quelldatensatz

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04727078