4-Pyridinecarboxaldehyde → HCID 67726470, compound

Temperature

-30 °C

n-Butyllithium (25 ml of a 1.6M solution in hexane, 40 mmol) was added dropwise to a stirred suspension of 2-hydroxyethyltriphenylphosphonium bromide (7.74 g, 20 mmol) in THF (50 ml) at −70° C. and the mixture allowed to warm to −30° C. and stirred for 2 hours. 4-Pyridinecarboxaldehyde (2.16 g, 20 mmol) was added to the resulting red solution and the mixture stirred for 1 hour at −30° C. and then cooled to −70° C. n-Butyllithium (12.5 ml of a 1.6M solution in hexane, 20 mmol) was added and the reaction mixture stirred at −70° C. for 1 hour. The mixture was quenched with isopropanol and allowed to warm to ambient temperature. Saturated aqueous ammonium chloride solution was added, the organic layer separated and the aqueous layer extracted with ethyl acetate (3×50 ml). The combined extracts were washed with brine and dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by column chromatography eluting with ethyl acetate to give 4-(3-hydroxyprop-2-en-1-yl)pyridine

1. stirringthe mixture stirred for 1 hour at −30° C.
2. additionwas added
3. stirringthe reaction mixture stirred at −70° C. for 1 hour
4. customThe mixture was quenched with isopropanol
5. temperatureto warm to ambient temperature
6. additionSaturated aqueous ammonium chloride solution was added
7. customthe organic layer separated
8. extractionthe aqueous layer extracted with ethyl acetate (3×50 ml)
9. washThe combined extracts were washed with brine
10. dry with materialdried (MgSO4)
11. customthe volatiles removed by evaporation
12. customThe residue was purified by column chromatography
13. washeluting with ethyl acetate

ORD record

ord-8ce5664bece649e49fd04ddd24080da8

Source dataset

uspto-grants-2002_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06362336B1