Triphenylphosphine → HCID 23506266, compound

3-(Pyridin-3-yl)-1-propanol (12.3 g, 90 mmol) and triphenylphosphine (34.0 g, 130 mmol) are dissolved in THF (200 ml), and thereto are added successively with stirring diisopropyl azodicarboxylate (22.2 g, 110 mmol) and 2-bromo-3-hydroxypyridine (12.0 g, 69 mmol) under ice-cooling. The mixture is stirred at room temperature for 30 minutes, and then the reaction solution is concentrated under reduced pressure. To the residue is added ethyl acetate (300 ml), and the mixture is extracted with a 10% aqueous hydrochloric acid solution (150 ml×2). The pH value of the aqueous layer is adjusted with potassium carbonate to pH 12, and the mixture is extracted with ethyl acetate (200 ml×2). The organic layer is washed with a saturated brine (50 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give the title compound (18.3 g) as a colorless oil.

1. temperaturecooling
2. concentrationthe reaction solution is concentrated under reduced pressure
3. additionTo the residue is added ethyl acetate (300 ml)
4. extractionthe mixture is extracted with a 10% aqueous hydrochloric acid solution (150 ml×2)
5. extractionthe mixture is extracted with ethyl acetate (200 ml×2)
6. washThe organic layer is washed with a saturated brine (50 ml×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD record

ord-366bd740838645249872467d2cd07566

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06765095B2