Water → Furo[2,3-b]pyridin-3-yl-acetic acid ethyl ester

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Reaction Steps

To a suspension of 0.325 g (8.14 mmol) of sodium hydride (50% suspension in mineral oil) in 8 ml of anhydrous tetrahydrofuran was added 0.1 ml of 1,1,1,3,3,3-hexamethyldisilazane and 1.81 g (8.14 mmol) of triethyl phosphonoacetate (Aldrich) in 4 ml of anhydrous tetrahydrofuran. The resulting mixture was stirred at room temperature for 1 h, cooled at 0° C. and there was added 1 g (7.4 mmol) of furo[2,3-b]pyridin-3-one (prepared according to J. Het. Chem. 1986, 23, 1465-1469). After being stirred at room temperature for 24 h, water was added, the mixture was extracted with dichloromethane. The organic phase was dried and evaporated to give crude product, which was purified by silica gel chromatography, eluting with ethyl acetate/cyclohexane in the proportions 40/60 to give 0.73 g of pure product.

Provenance & Evidence