2,3-Diethyl 2,3-pyridinedicarboxylate → Ethyl 2-formylnicotinate

In flame-dried glassware under N2 atmosphere, to a solution of 2,3-pyridinedicarboxylic acid diethyl ester (0.254 g, 1.14 mmol) in anhydrous tolune (5 mL) at -78° C. was added diisobutylaluminum hydride (DiBal) (1.48 mL, 1.48 mmol, 1M in tolune). After 30 minutes, additional DiBal (0.4 mL, 0.4 mmol, 1M in toluene) was added. After 15 minutes, the reaction mixture was quenched with methanol (2 mL)/saturated Na/K tartrate (40 mL) and extracted into EtOAc (3×50 mL). The combined organic extracts were washed with saturated NaHCO3 (2×50 mL), saturated brine (1×75 mL), dried over MgSO4, filtered, concentrated, and flash chromatographed (5 to 10% EtOAc/CH2Cl2 gradient) to provide 0.075 g of the title compound as a colorless oil (36.8%).

1. waitAfter 15 minutes
2. customthe reaction mixture was quenched with methanol (2 mL)/saturated Na/K tartrate (40 mL)
3. extractionextracted into EtOAc (3×50 mL)
4. washThe combined organic extracts were washed with saturated NaHCO3 (2×50 mL), saturated brine (1×75 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customflash chromatographed (5 to 10% EtOAc/CH2Cl2 gradient)

ORD record

ord-d3352480148d4026898f0254f5a1ab26

Source dataset

uspto-grants-1991_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04983612