Furfural → 2-[2-{3-Pyridyl}ethenyl]furan

To a stirred -78° C. solution of diethyl 3-pyridylmethylphosphonate (3.0 g, 13 mmol), prepared as in step 3, in THF (50 mL) was added n-butyllithium (25 mL, 55 mmol, 2.5M in hexanes). The cold reaction mixture was stirred 0.5 hours followed by the slow addition of furfuraldehyde (1.24 g, 13 mmol). The reaction was stirred 2 hours at -78° C. and the ice bath removed and allowed to stir at ambient temperature overnight. Saturated NH4Cl was added and the mixture was diluted with ether. The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate-hexanes to afford 1.1 g of 2-[2-{3-pyridyl}ethenyl]furan.

1. customThe cold reaction mixture
2. stirringThe reaction was stirred 2 hours at -78° C.
3. customthe ice bath removed
4. stirringto stir at ambient temperature overnight
5. additionSaturated NH4Cl was added
6. additionthe mixture was diluted with ether
7. washThe organic layer was washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. customThe resulting residue was purified by column chromatography on silica gel eluting with 40% ethyl acetate-hexanes

ORD record

ord-4c02adb219a64e2d93e161c0c37f0e09

Source dataset

uspto-grants-1997_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05616596