Hydrogen iodide → Ethyl 6-hydroxymethyl-4-iodopyridine-2-carboxylate

Participants

Reaction Steps

Compound 1 (5.24 g, 15.0 mmol) was dissolved in EtOH (270 ml) at 40° C. NaBH4 (0.57 g, 15 0 mmol) was carefully added and the mixture stirred for 40 min. The reaction was stopped by adjusting the pH to 3 with 28% (w/w) aqueous hydriodic acid. The mixture was neutralized with saturated NaHCO3 solution and evaporated to dryness. The residue was suspended in water (150 mL) and the product was extracted from the aqueous phase with 10% EtOH/CH2Cl2 solution (3×150 ml). The combined organic fractions were dried with Na2SO4 and evaporated to dryness. Purification on silica gel (petroleum ether, by 40-60° C./ethyl acetate 2:5) yielded 2.89 g (63%) of the title compound.

Provenance & Evidence