Pyridine → (3-Phenyl-5-isoxazolyl)methanol

Temperatur

0 °C

(Z)-Benzaldehyde oxime (3.4 g, 28.2 mmol) was dissolved in anhydrous THF (50 mL) and cooled to 0° C. N-Chlorosuccinimide (5.63 g, 42.3 mmol) and pyridine (221 mg, 2.8 mmol) were added and the mixture was stirred at room temperature for 1 hour. Prop-2-yn-1-ol (1.89 g, 33.4 mmol) and NEt3 (286 mg, 2.8 mmol) were added and the mixture was heated at reflux for 2 hours. The reaction was cooled and quenched with water, extracted with EtOAc and dried over anhydrous sodium sulfate. The solution was concentrated under vacuum to give a crude product, which was purified by column chromatography to afford (3-phenylisoxazol-5-yl)methanol as a white solid (1.8 g).

1. temperaturethe mixture was heated
2. temperatureat reflux for 2 hours
3. temperatureThe reaction was cooled
4. customquenched with water
5. extractionextracted with EtOAc
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationThe solution was concentrated under vacuum
8. customto give a crude product, which
9. customwas purified by column chromatography

ORD-Eintrag

ord-fa32c6c8264a4fdcb326fb12add69af1

Quelldatensatz

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08969349B2