With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.25637-16-5,4-Bromotetrahydropyran,as a common compound, the synthetic route is as follows.
General procedure: To a flame-dried Schlenk tube was charged with vinyl bromide (0.30 mmol, 2 equiv, if solid), unactivated alkyl halide (0.15 mmol, if solid), zinc powder (16.5 mg, 0.30 mmol, 2 equiv), and MgCl2 (14.2 mg, 0.15mmol, 1 equiv). The tube was moved into a dry glovebox, at which point Ni(cod)2 (2.1 mg, 0.008 mmol, 5 mol%) was added. The tube was capped with a rubber septum, and it was moved out of the glovebox. At this point, the vinyl bromide (0.30 mmol, 2 equiv, if liquid) and alkylhalide (0.15 mmol, 1 equiv, if liquid) were added together with solvent (1 mL) and pyridine (11.8 mg, 0.15 mmol, 1 equiv) via a syringe.The mixture was stirred for 16 h under N2 atmosphere at 25 C, and then it was directly loaded onto a column (silica gel) without work-up. The residue in the reaction vessel was rinsed with small amount of CH2Cl2. Flash column chromatography provided the product as a solid or oil. The E/Z ratio of the product was determined by GC-MS. (E)-4-Styryl-1-tosylpiperidine (3): according to the general procedure, column chromatography (silica gel, 7% EtOAc/PE) gave the product (42.5 mg, 0.125 mmol, 83%) as a white solid; mp 140-141 C. 1H NMR (500 MHz, CDCl3): delta = 7.66 (d, J = 8.0 Hz, 2 H), 7.34-7.28 (m, 6 H), 7.20 (t, J = 7.0 Hz, 1 H), 6.31 (d, J = 16.0 Hz, 1 H), 5.97 (dd, J = 7.0,16.0 Hz, 1 H), 3.82-3.80 (m, 2 H), 2.44 (s, 3 H), 2.34-2.29 (m, 2 H), 2.08-2.02 (m, 1 H), 1.83-1.81 (m, 2 H), 1.73-1.70 (m, 1 H), 1.46-1.39 (m, 1 H). 13C NMR (125 MHz, CDCl3): delta = 143.4, 137.1, 133.4, 133.1, 129.5, 128.9, 128.5, 128.2, 127.7, 127.2, 126.0, 46.1, 38.5, 31.2, 21.5. HRMS (ESI): m/z [M + H]+ calcd for C20H24NO2S: 342.1522; found: 342.1525.
25637-16-5, The synthetic route of 25637-16-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Gu, Jun; Qiu, Canbin; Lu, Wenbin; Qian, Qun; Lin, Kunhua; Gong, Hegui; Synthesis; vol. 49; 8; (2017); p. 1867 – 1873;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics