4-Nitrophenol → 2-Acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester

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Reaction Steps

2-(1,1-Dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid (0.66 g), p-nitrophenol (0.32 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.49 g) and 4-dimethylaminopyridine (catalytic) in dry dichloromethane (40 ml) were stirred overnight at room temperature. The mixture was diluted with dichloromethane (50 ml), washed with water (100 ml), dried over magnesium sulfate, filtered and the solvent removed in vacuo. Purification by column chromatography on silica eluting with 33% hexane in ethyl acetate to 100% ethyl acetate gave 2-(1,1-dimethoxyethyl)-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.51 g) and 2-acetyl-7-methoxyfuro[2,3-c]pyridine-4-carboxylic acid 4-nitrophenyl ester (0.20 g) as white solids.

Provenance & Evidence