Synthesis
2-Allylphenol (5) (200 mg, 1.49 mmol) was used as a raw material, which was mixed with m-chloroperoxybenzoic acid (616 mg, 3.57 mmol) in dichloromethane (DCM, 30 mL) and the reaction was stirred for 6 hours at room temperature. Subsequently, potassium carbonate (K2CO3, 617 mg, 4.47 mmol) and methanol (25 mL) were added to the reaction system and stirring was continued for 14 hours. After completion of the reaction, the solvent was removed by evaporation and diluted by adding water (15 mL). The mixture was extracted with dichloromethane (3 x 20 mL), the organic phases were combined, washed with brine (10 mL), dried over anhydrous sodium sulfate (Na2SO4), and the solvent was evaporated again. The crude product was purified by fast column chromatography (eluent: ethyl acetate/hexane=1:7) to afford the target compound (2,3-dihydrobenzofuran-2-yl)methanol (6) (195 mg, 87% yield) as a light yellow oil. The structure of the product was confirmed by 1H NMR (CDCl3, 300 MHz) and FTIR (neat): 1H NMR δ 7.17 (d, 1H, J = 7.4 Hz), 7.11 (t, 1H, J = 7.6 Hz), 6.85 (t, 1H, J = 7.4 Hz), 6.79 (d, 1H, J = 7.4 Hz), 4.91 (m, 1H) , 3.85 (dd, 1H, J = 12.0, 3.2 Hz), 3.74 (dd, 1H, J = 12.0, 6.3 Hz), 3.25 (dd, 1H, J = 15.5, 9.4 Hz), 3.01 (dd, 1H, J = 15.5, 7.4 Hz); FTIR 3391, 3049, 1047 cm-1.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 12, p. 2545 - 2549
[2] Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2685 - 2689
[3] Bioorganic and medicinal chemistry letters, 1999, vol. 9, # 3, p. 401 - 406
[4] Tetrahedron Asymmetry, 2000, vol. 11, # 16, p. 3375 - 3393
[5] Synthesis (Germany), 2017, vol. 49, # 18, p. 4254 - 4260
