Ethyl formate → 3-Hydroxy-2-pyridin-3-yl-acrylic acid ethyl ester

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Reaction Steps

1.65 g (10.0 mmol) 3-pyridylacetic acid ethyl ester are initially introduced into 20 ml anhydrous toluene under argon. 410 mg (10.3 mmol) sodium hydride suspension (60% strength in paraffin oil) and 130 mg (0.50 mmol) 18-crown-6 are added in portions to the solution and the mixture is stirred at RT for 30 min and then at 85° C. (bath temperature) for 30 min. After this time, the mixture is cooled and 1.48 g (20.0 mol) formic acid ethyl ester are added dropwise at approx. 20° C. The mixture is stirred first at RT for 60 min and then at 90° C. (bath temperature) for 60 min. After cooling, the reaction solution is introduced on to approx. 50 ml saturated ammonium chloride solution and extracted with ethyl acetate (five times with 40 ml each time). The combined organic phases are washed with 50 ml saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The solid obtained is washed with pentane and dried in vacuo.

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