Synthetic Route of 6971-51-3 ,Some common heterocyclic compound, 6971-51-3, molecular formula is C8H10O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.
3-methoxybenzyl alcohol (248 mu, 2.0 mmol) and triethylamine (335 mu, 2.4 mmol) were dissolved in anh. DCM (7 mL). Thionyl chloride (218 mu, 3.0 mmol) was added slowly. The reaction mixture was stirred at RT. for 1 h. The reaction mixture was washed with an aqueous solution of HCI 1 N. The organic phase was dried over MgS04. The solvent was removed under reduced pressure to give the desired 2-methoxybenzyl chloride (313 mg, 100 %) as a yellowish oi l . 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid (example 74, 85 mg, 0.26 mmol) was dissolved in anhydrous DMF (1 mL) then cesium carbonate (169 mg, 0.52 mmol) and 3-methoxybenzyl chloride (81 mg, 0.52 mmol) were added. The reaction mixture was stirred at r.t. for 18 h. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine and dried over MgS04. The solvent was removed under reduced pressure. Purification of the crude by flash chromatography using a mixture of Cyclohexane/EtOAc (8/2) as eluent gave the desired (3- m e t h o x y p h e n y l ) m e t h y l 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl-2-oxo-3,4- dihydropyridine-5-carboxylate as a yellowish oil (1 1 mg, 9 %). 1 H N MR (300 MHz, CDCI3) delta 2.62 (s,3H), 2.71 (dd, J = 15.8, 2.2 Hz, 1 H), 2.92 (dd, J = 15.8, 7.5 Hz, 1 H), 3.31 (s, 3H), 3.37 (ddd, J = 10.0, 8.5, 3.6 Hz, 1 H), 3.46 (dt, J = 10.0, 4.1 Hz, 1 H), 3.70-3.79 (m, 4H), 4.13-4.23 (m, 2H), 5.04 (d, J = 12.7 Hz, 1 H), 5.1 1 (d, J = 12.7 Hz, 1 H), 6.64(s, 1 H), 6.70 (d, J = 7.5, 1 H), 6.81 (dd, J = 8.2, 2.5 Hz, 1 H), 7.10 (d, J = 8.4 Hz, 2H), 7.16-7.23 (m,3H). MS [M+H]+ 444. HRMS : calcd for C24H27N05CI, [M+H]+ 444.1578, found 444.1579.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 6971-51-3, (3-Methoxyphenyl)methanol, other downstream synthetic routes, hurry up and to see.
Reference:
Patent; UNIVERSITE DE LILLE 2 DROIT ET SANTE; INSTITUT PASTEUR DE LILLE; INSERM (INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE); CHARTON, Julie; DEPREZ, Benoit; LEROUX, Florence; STAELS, Bart; MUHR-TAILLEUX, Anne; HENNUYER, Nathalie; LESTAVEL, Sophie; PICON, Sylvain; AKNIN, Karen; BOULAHJAR, Rajaa; DUBANCHET, Barbara; (234 pag.)WO2016/16238; (2016); A1;,
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