3-Pyridinecarboxaldehyde → 3-(Oxiran-2-yl)pyridine

Temperatur

0 °C

To a solution of 2.59 g of 3-pyridinecarboxaldehyde and 62 mg of tetra-n-butylammonium bromide in 60 mL CH2Cl2 at room temperature is added a solution of 10.0 g of trimethylsulfonium methylsulfate in 15 mL H2O. The resulting solution is set stirring and cooled to 0° C. Aqueous NaOH (50% w/w; 40 mL) is added in portions while stirring and the mixture subsequently refluxed for 1 h. After cooling to room temperature, the mixture is filtered and the filtrate extracted with CH2Cl2. The combined extracts are dried over MgSO4, filtered, and concentrated to yield a red oil, which is subjected to Kugelrohr distillation under high vacuum at 150° C. to yield 838 mg of the title compound as a clear, light yellow oil.

1. stirringwhile stirring
2. temperaturethe mixture subsequently refluxed for 1 h
3. temperatureAfter cooling to room temperature
4. filtrationthe mixture is filtered
5. extractionthe filtrate extracted with CH2Cl2
6. dry with materialThe combined extracts are dried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated
9. customto yield a red oil, which
10. distillationis subjected to Kugelrohr distillation under high vacuum at 150° C.

ORD-Eintrag

ord-80408188b07545bfbcf381ecf1bc3f7b

Quelldatensatz

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06852731B2