Ethyl Acetate → 2-Methylpyridine-3-carbaldehyde

Temperature

0 °C

A solution of methyl 2-methylnicotinate (0.5 g, 3.3 mmol) in THF (16 mL) at 0° C. was treated dropwise with lithium aluminum hydride in THF (6.6 mL, 1 M), stirred at 0° C. for 1.5 hours, treated with ethyl acetate (3 mL), warmed to 25° C., and partitioned between ethyl acetate and saturated NaHCO3. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated. A solution of the residue (0.391 g) in dichloromethane (16 mL) was treated with MnO2 (2 g), stirred at 25° C. for 68 hours, filtered through celite®, and the solvent was evaporated to give the title compound (0.303 g, 75% yield), which was used without further purification.

1. temperaturewarmed to 25° C.
2. custompartitioned between ethyl acetate and saturated NaHCO3
3. washThe organic phase was washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. additionA solution of the residue (0.391 g) in dichloromethane (16 mL) was treated with MnO2 (2 g)
8. stirringstirred at 25° C. for 68 hours
9. filtrationfiltered through celite®
10. customthe solvent was evaporated

ORD record

ord-ff97ec31e6454d38bdd3edd780893ac2

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834043B2