Ethyl Acetate → 6-Methyl-3-pyridinecarboxaldehyde

Temperature

0 °C

A solution of methyl 6-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), and stirred at 25° C. The reaction was partitioned between ethyl acetate and saturated NaHCO3, and the organic phase was washed with brine and dried over MgSO4, filtered and concentrated. A solution of the residue (0.395 g) in dichloromethane (16 mL) was treated with MnO2 (2 g), stirred at 25° C. for 68 hours, and filtered through celite® to give the title compound (0.326 g, 80% yield), which was used without further purification.

1. stirringstirred at 25° C
2. customThe reaction was partitioned 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 (0.395 g) in dichloromethane (16 mL) was treated with MnO2 (2 g)
8. stirringstirred at 25° C. for 68 hours
9. filtrationfiltered through celite®

ORD record

ord-13c737cfd670472993cd02ddc3f06d8d

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07834043B2