With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.33821-94-2,2-(3-Bromopropoxy)tetrahydro-2H-pyran,as a common compound, the synthetic route is as follows.
To a solution of (Z)-phenyl N’-cyano-N-(3,4-difluorophenyl)carbamimidate (286 mg, 1.05 mmol) and 2-(3-bromopropoxy)tetrahydro-2H-pyran (369 mg, 277 mu, 1.57 mmol) in DMF (10.5 mL) was added at room temperature under an athmosphere of nitrogen potassium carbonate (289 mg, 2.09 mmol). The suspension was heated to 85C over night. Additional 2-(3- bromopropoxy)tetrahydro-2H-pyran (140 mu, 0.8mmol) und potassium carbonate (145 mg, 1.05 mmol) was added and the reaction was heated for 5 hours to 85C. Water was added and the reaction was extracted twice with diethyl ether. The combined organic layers were washed with water and with saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and the solvent was evaporated under reduced pressure. The title compound was obtained as a light yellow viscous oil (202 mg, 46%) after column chromatography on silica gel using a gradient of heptane/ethyl acetate 4: 1 to 1 : 1 (v/v) as eluent.MS ISP (m/e): 332.1 (100) [(M-THP+H)+], 416.3 (5) [(M+H)+].1H NMR (DMSO-D6, 300 MHz): delta (ppm) = 7.38 (t, 2H), 7.26 – 7.16 (m, 3H), 7.05 (m, 3H), 4.52 (t, 1H), 3.97 (t, 2H), 3.85 (m, 2H), 3.48 (m, 2H), 2.00 (pent, 2H), 1.79 (m, 1H), 1.68 (m, 1H), 1.55 (m, 4H)).
33821-94-2, 33821-94-2 2-(3-Bromopropoxy)tetrahydro-2H-pyran 2777988, aTetrahydropyrans compound, is more and more widely used in various fields.
Reference£º
Patent; F. HOFFMANN-LA ROCHE AG; BAUMANN, Karlheinz; GOETSCHI, Erwin; GREEN, Luke; JOLIDON, Synese; KNUST, Henner; LIMBERG, Anja; LUEBBERS, Thomas; THOMAS, Andrew; WO2011/92272; (2011); A1;,
Tetrahydropyran – Wikipedia
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