General procedure for the synthesis of 3-furanmethanol from ethyl 3-furancarboxylate: To a solution of ethyl 3-furancarboxylate (7) (4.00 g, 28.5 mmol) in anhydrous ethyl ether (Et2O, 140 mL) was added lithium aluminum hydroxide (LiAlH4, 1.62 g, 42.8 mmol) batchwise at 0 °C. The reaction mixture was stirred at room temperature for 45 min. Subsequently, the reaction was quenched by sequential addition of water (H2O, 2 mL), 1 M sodium hydroxide (NaOH, 2 mL) and water (H2O, 6 mL) at 0 °C. The resulting white precipitate was removed by filtration and the solvent was removed by distillation under reduced pressure to give 3-furan methanol (8) (2.60 g, 93%) as a pale yellow oil. Thin layer chromatography (TLC) Rf value was 0.2 (unfolding agent: hexane/ethyl acetate, 4:1).1H NMR (CDCl3) δ: 7.42-7.41 (m, 1H, H2), 7.40-7.39 (m, 1H, H5), 6.44-6.42 (m, 1H, H4), 4.55 (s, 2H, CH2), 1.81 (br s. 1H, OH).13C NMR (CDCl3) δ: 143.3 (C5), 139.9 (C2), 125.1 (C3), 109.9 (C4), 56.1 (CH2). High Resolution Mass Spectrometry (HRMS-EI): m/z [M]+ calculated value for C5H6O2: 98.0368, measured value: 98.0371.
