Dimethylformamide → 6-Methyl-3-pyridinecarboxaldehyde

To a solution of 5-bromo-2-methylpyridine (151; 10 g, 58.1 mmol) in THF (150 mL) was added n-BuLi (2.5 M, 25.6 mL) at −78° C. The reaction mixture was stirred at this temperature for 1 h. DMF (1.30 mL) was then added and the resulting reaction mixture was stirred for 1 h at −78° C. The reaction was quenched by the addition of aq. NH4Cl. Upon warming to room temperature, the mixture was extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 6-methylnicotinaldehyde 152 (5.0 g, 72%).

1. customthe resulting reaction mixture
2. stirringwas stirred for 1 h at −78° C
3. customThe reaction was quenched by the addition of aq. NH4Cl
4. extractionthe mixture was extracted with EtOAc
5. dry with materialThe combined organic layers were dried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe resulting residue was purified by chromatography

ORD-Eintrag

ord-2b79cc6d18e6464aaf106b76420e7363

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846947B2