Acetonitrile → 3-Hydroxy-3-(pyridin-4-yl)propanenitrile

Temperatur

0 °C

Diisopropylamine (1.98 g, 19.6 mmol) was added dropwise to a solution of butyllithium/hexane (10.5 ml, 16.8 mmol) in anhydrous tetrahydrofuran (20 ml) at −80° C. over five minutes, the temperature was raised to 0° C., and the mixture was stirred for 30 minutes. The mixture was cooled to −80° C., then acetonitrile (573 mg, 14.0 mmol) was added dropwise to the mixture over seven minutes, and further after 20 minutes, 4-pyridinecarboxyaldehyde (758 mg, 7.08 mmol) was added dropwise thereto over 10 minutes. After 50 minutes, a saturated aqueous ammonium chloride solution (20 ml) was added to the reaction mixture, and the temperature was raised to room temperature. The whole was continuously extracted (ethyl acetate and water) for four days. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give 3-hydroxy-3-(4-pyridyl)propionitrile (666 mg, colorless crystals, 63.5%).

1. temperatureThe mixture was cooled to −80° C.
2. waitfurther after 20 minutes
3. addition4-pyridinecarboxyaldehyde (758 mg, 7.08 mmol) was added dropwise
4. waitover 10 minutes
5. waitAfter 50 minutes
6. temperaturethe temperature was raised to room temperature
7. extractionThe whole was continuously extracted (ethyl acetate and water) for four days
8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
9. customthe solvent was evaporated under reduced pressure
10. customthe residue was purified by silica gel column chromatography

ORD-Eintrag

ord-a39f48e6c13347f7964bb391a1bee50f

Quelldatensatz

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07741346B2