Hydrochloric Acid → Ethyl 3-[6-(2-fluorophenyl)pyridin-3-yl]propanoate

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Reaction Conditions

Reaction Steps

Under nitrogen, 16.26 g (0.06 mol) of 3-[6-(2-fluoro-phenyl) -pyridin-3-yl]-acrylic acid ethyl ester were dissolved in 500 ml of 95% ethanol and cooled to 5 to 10° C. After addition of 9.42 g (0.03 mol) of bismuth trichloride, a total of 9.12 g (0.24 mol) of sodium borohydride was added in portions over 45 min. The resulting mixture was stirred at 15 to 20° C. for 1 h, then cooled to 10° C. and poured onto ice/water. The pH was adjusted to 7 with 2 N hydrochloric acid, dichloromethane was added, and the precipitated salts were separated by filtration. The organic phase of the mother liquor was separated, and the aqueous phase extracted once with dichloromethane. The combined organic phases were washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and evaporated to dryness. The remaining solid was purified by chromatography (silica gel, n-heptane/ethyl acetate 3:1). Yield: 11.5 g.

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