Diethyl 2-[2-(4-pyridyl)ethyl]malonate → Methyl 4-(Pyridin-4-yl)butanoate

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Reaction Steps

A solution of diethyl β-(4-pyridyl)-ethylmalonate (25 g, 94 mmol) in ethanol (100 mL) and NaOH (1M, 200 mL) was refluxed for 2 hours. The ethanol was removed by distillation, and the solution was acidified with concentrated H2SO4. The resulting solution was refluxed for 30 minutes, and the pH was adjusted to 4. The solvent was removed and the residue was dried under vacuum. The residue was taken up in methanol (300 mL), trimethyl orthoformate (10 mL) and H2SO4 (5 mL), and the resulting solution was refluxed for 3 hours. The solvent was removed, and the residue was taken up in CHCl3 and extracted with NaOH (1M) and saturated brine, dried (Na2SO4) and evaporated to yield methyl 4-(4-pyridyl)butanoate (48) (15 g).

Provenance & Evidence