Potassium Carbonate → Ethyl 3-chloro-6-benzofurancarboxylate

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Reaction Steps

trans-Methyl 2,3-dichloro-2,3-dihydro-1-benzofuran-6-carboxylate (58 mg, 0.23 mmol) is dissolved in EtOH (2 ml), treated with K2CO3 (187 mg, 1.35 mmol) and stirred at RT overnight. The mixture is concentrated to dryness, the residue is dissolved in 50% saturated NaCl (10 ml) and extracted with CH2Cl2 (3×10 ml). The combined organics are dried (K2CO3), filtered, and concentrated in vacuo to a yellow oil. The crude material is chromatographed over 10 g slurry-packed silica gel, eluting with 25% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 30 mg (58%) of ethyl 3-chloro-1-benzofuran-6-carboxylate as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 1.44, 4.43, 7.66, 7.79, 8.07, 8.21 ppm.

Provenance & Evidence