With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.53911-68-5,4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione,as a common compound, the synthetic route is as follows.
Commercial 4-bromo-l,2-phenylenediamine (561 mg) and 3-(4-chlorophenyl)- glutaric anhydride (674 mg) were dissolved in THF (1 ml) with heating. The dark solution was stirred at rt for 1 h. Then the solution was decolourised with activated carbon and filtered. The filtrate was concentrated and the solid residue dried in vacuo. The solid was dissolved in a mixture of acetic acid (4 ml) and cone. HCI (2 ml) and stirred under reflux for 3 h. All volatiles were removed at the water aspirator and the residue was recrystallised from ethanol/EtOAc 1 : 3 to give a crude (0.47 g). The impure crude was again refluxed with acetic acid/cone. HCI 2: 1 for 1 h to leave after concentration and acetone trituration 4-(5-bromo-2- benzimidazolyl)-3-(4-chlorophenyl)butanoic acid HCI (0.3 g) as light greyish solid.1H-NMR (500 MHz, DMSOd6): delta (ppm) = 2.72 (dd, J = 16.2, 8.6 Hz, IH), 2.83 (dd, J = 16.3, 8.2 Hz, IH), 3.43 (dd, J = 14.9, 9.2 Hz, IH), 3.55 (dd, J = 14.9, 6.9 Hz, IH), 3.85 (m, IH), 7.30 (d, J = 8.5 Hz, 2H), 7.35 (d, J = 8.5 Hz, IH), 7.60 (dd, J = 8.7, 1.7 Hz, IH), 7.67 (d, J = 8.7 Hz, IH), 7.94 (d, J = 1.7 Hz, IH). 13C-NMR and DEPT (125 MHz, DMSOd6) : delta (ppm) = 32.66 (CH2), 39.19 (CH),39.60 (CH2), 115.57 (CH), 116.42 (CH), 117.34 (C), 128.14 (CH), 128.34 (2 CH), 129.14 (2 CH), 130.26 (C), 131.44 (C), 132.32 (C), 140.69 (C), 153.07 (C), 172.12 (CO). MS ( + ESI) : m/z = 393 (M + H).
53911-68-5 4-(4-Chlorophenyl)dihydro-2H-pyran-2,6(3H)-dione 104639, aTetrahydropyrans compound, is more and more widely used in various.
Reference£º
Patent; UNIVERSITAET DES SAARLANDES; ENGEL, Matthias; FROeHNER, Wolfgang; STROBA, Adriane; BIONDI, Ricardo M.; WO2010/43711; (2010); A1;,
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