[Synthesis]
Procedure: synthesis of (2,3-dihydrobenzofuran-6-yl)methanol; A THF solution of methyl 2,3-dihydrobenzofuran-6-carboxylate (17.8 g, 100 mmol) was slowly added to a stirred tetrahydrofuran (THF, 300 mL) solution of lithium aluminium hydride (6.1 g, 250 mmol) at 0 °C. The reaction mixture was continued to be stirred at room temperature for 1 hour. Upon completion of the reaction, the reaction was quenched by careful addition of saturated aqueous sodium hydroxide solution, followed by extraction of the mixture with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford (2,3-dihydrobenzofuran-6-yl)methanol (13.8 g, 92.0% yield). The product was characterized by 1H NMR (400 MHz, CDCl3): δ 7.17 (d, J = 7.2 Hz, 1H), 6.84 (d, J = 7.2 Hz, 1H), 6.81 (s, 1H), 4.62 (s, 2H), 4.58 (t, J = 8.4 Hz, 2H), 3.20 (t, J = 8.4 Hz, 2H), 1.67 ( br s, 1H). |