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.,53911-68-5
The solution of 4-chloro-1,2-phenylenediamine (2.85 g) and 3-(4-chlorophenyl)-glutaric anhydride (4.49 g) in 1,4-dioxane (7 ml) was stirred at rt for 1 h. The precipitate is collected by suction filtration, washed with 1,4-dioxane, and dried in vacuo to provide a mixture of regioisomeric amides (5.37 g) as beige coloured solid.This solid is dissolved in acetic acid (10 ml) with heating. Conc. HCl (4 ml) is added and the resulting solution is heated to reflux for 2 h. Then all volatiles are removed at the water aspirator and the still hot residue is suspended in acetone (20 ml). The suspension is cooled to rt with stirring and the solid is isolated by filtration. After washings with acetone the off- white solid is dried in vacuo to yield the hydrochloride salt of 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)butanoic acid (4.66 g).1H-NMR (500 MHz, DMSO-d6): delta (ppm)=2.72 (dd, J=16.2, 8.6 Hz, 1H), 2.83 (dd, J=16.2, 6.2 Hz, 1H), 3.43 (dd, J=14.9, 9.2 Hz, 1H), 3.55 (dd, J=14.9, 6.9 Hz, 1H), 3.86 (m, 1H), 7.30 (d, J=8.5 Hz, 2H), 7.36 (d, J=8.5 Hz, 1H), 7.48 (dd, J=8.8, 1.9 Hz, 1H), 7.73 (d, J=8.8 Hz, 1H), 7.81 (d, J=1.8 Hz, 1H).13C-NMR and DEPT (125 MHz, DMSO-d6): delta (ppm)=32.67 (CH2), 39.19 (CH), 39.60 (CH2), 113.55 (CH), 115.25 (CH), 125.51 (CH), 128.34 (2CH), 129.14 (2CH), 129.56 (C), 129.96 (C), 131.43 (C), 131.92 (C), 140.70 (C), 153.27 (C), 172.11 (CO). MS (+ESI): m/z=349 (M+H).
The synthetic route of 53911-68-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
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