Nicotinoyl chloride → Ethyl 3-oxo-3-(pyridin-3-yl)-2-(thiophen-3-yl)propanoate

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Reaction Steps

To a solution of ethyl 2-(thiophen-3-yl)acetate (2.3 g, 16.2 mmol) in anhydrous THF (20 mL) was added LiHMDS (19.4 mL, 19.44 mmol) at −78° C. After stirring at that temperature for 0.5 h, a solution of nicotinoyl chloride (2.8 g, 16.2 mmol) in anhydrous THF (10 mL) was added into the reaction mixture and stirred at −78° C. for 4 hours. The mixture was quenched with NH4Cl solution, extracted with EtOAc. The organic layer was concentrated in vacuo and purified by silica gel column chromatography (1.7 g, yield 38%).

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