Synthesis
5-Hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (14.20 g, 100 mmol) was dissolved in methanol (100 mL) and a solution of sodium hydroxide (4.40 g, 110 mmol) in water (10 mL) was added. The reaction mixture was heated to reflux. Subsequently, benzyl chloride (13.92 g, 110 mmol) was added slowly and dropwise over 30 minutes and the reaction was kept at reflux for 18 hours. Upon completion of the reaction, the reaction mixture was concentrated and the residue was extracted by adding dichloromethane (400 mL) to the residue. The inorganic salts were removed by filtration. The dichloromethane layer was washed sequentially with 5% sodium hydroxide solution (100 mL) and water (100 mL), then dried with anhydrous sodium sulfate, filtered and concentrated the filtrate, and finally recrystallized by ethanol to give the light yellow solid product 5-(benzyloxy)-2-(hydroxymethyl)-4H-pyran-4-one (19.26 g, 83% yield).
References
[1] Tetrahedron Letters, 2010, vol. 51, # 38, p. 5038 - 5040
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 7, p. 2669 - 2684
[3] Heterocycles, 2013, vol. 87, # 6, p. 1349 - 1358
[4] Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 9, p. 1647 - 1655
[5] European Journal of Medicinal Chemistry, 2016, vol. 115, p. 132 - 140
