Synthetic Route of 2425-41-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 2425-41-4, name is (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol. A new synthetic method of this compound is introduced below.
under argon at 0 oC was added a solution of diol (S109, 4.92 g, 22.0 mmol) in THF (20 mL) dropwise; the resulting mixture was warmed to room temperature and stirred for 1h. The reaction mixture was cooled to 0 oC, a solution of propargyl bromide (18.6 g, 158.4 mmol) in THF (25 mL) was added slowly, and the resulting mixture was warmed to room temperature and stirred overnight at 40 oC. After the product was consumed, as observed by TLC, the reaction was quenched by dropwise addition of water at 0 oC, and the resulting mixture was extracted with dichloromethane (50 mL x 2). The combined organic layers were washed with brine and dried over anhydrous Na2SO4, filtered, and evaporated to give a residue, which was purified by flash silica gel column using ISCO companion (hexane/ethyl acetate, 0 – 30%) to give 5.92 g (89.5%) of compound S110 as an oil.1H NMR (500 MHz, CDCl3; ppm): d7.49-7.47 (dd, J 8.0, 1.5 Hz, 2H), 7.38-7.34 (m, 3H), 5.43 (s, 1H), 4.21 (d, J 2.5 Hz, 2H), 4.12 (t, J 2.5 Hz, 4H), 4.10 (s, 1H), 3.91 (s, 1H), 3.89 (s, 1H), 3.37 (s, 2H); ESI MS for C18H20O4 calculated 300.34, observed [M+H]+ 301.3.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,2425-41-4, (2-Phenyl-1,3-dioxane-5,5-diyl)dimethanol, and friends who are interested can also refer to it.
Reference:
Patent; TOLLNINE, INC.; PONS, Jaume; WAN, Hong I.; BRADSHAW, Curt W.; SIM, Bang Janet; KUO, Tracy Chia-Chien; (239 pag.)WO2020/81744; (2020); A1;,
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