3-Methoxybenzyl chloride synthesis
- Product Name:3-Methoxybenzyl chloride
- CAS Number:824-98-6
- Molecular formula:C8H9ClO
- Molecular Weight:156.61
6971-51-3
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Yield:824-98-6 100%
Reaction Conditions:
with thionyl chloride;triethylamine in dichloromethane at 20; for 1 h;
Steps:
103 (3-methoxyphenyl)methyl 4-(4-chlorophenyl)-1 -(2-methoxyethyl)-6-methyl- 2-oxo-3,4-dihydropyridine-5-carboxylate
3-methoxybenzyl alcohol (248 μ, 2.0 mmol) and triethylamine (335 μ, 2.4 mmol) were dissolved in anh. DCM (7 mL). Thionyl chloride (218 μ, 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) δ 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.
References:
UNIVERSITE DE LILLE 2 DROIT ET SANTE;INSTITUT PASTEUR DE LILLE;INSERM (INSTITUT NATIONAL DE LA SANTÉ ET DE LA RECHERCHE MÉDICALE);CHARTON, Julie;DEPREZ, Benoit;LEROUX, Florence;STAELS, Bart;MUHR-TAILLEUX, Anne;HENNUYER, Nathalie;LESTAVEL, Sophie;PICON, Sylvain;AKNIN, Karen;BOULAHJAR, Rajaa;DUBANCHET, Barbara WO2016/16238, 2016, A1 Location in patent:Page/Page column 126-127
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824-98-6
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