With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1768-64-5,4-Chlorotetrahydropyran,as a common compound, the synthetic route is as follows.
[0001] A stirred mixture of (S)-(+)-prolinol (0.414 g, 3.99 mmol), NiCl2-glyme (0.449 g, 1.99mmol), phenyl boronic acid (3.04 g, 24.98 mmol) and KHMDS (6.6 g, 33.3 mmol) was submitted tofew cycles of vacuum/argon flow. i-PrOH (40 mL) was added and the resulting mixture was stirred atroom temperature for 10 min, then 4-chlorotetrahydropyran (1.75 mL, 16.6 mmol) was addeddropwise. The resulting yellowish mixture was heated at 65 C for 50 h, then cooled at roomtemperature, diluted with EtOAc (200 mL) and washed with 10 % HCl solution (30 mL), sat. NaHCO3solution (30 mL x 2) and brine (40 mL). The organic layer was dried over Na2SO4, filtered andconcentrated to dryness to afford a solid crude (2.5 g). Purification by typical silica gel flashchromatography using a Teledyne ISCO apparatus (cyclohexane/TBME from 100:0 to 80:20) affordedthe pure title compound (1.29 g, 48%), as a liquid. Rt = 2.36 min. 1H NMR (CDCl3): delta 7.40-7.28 (m,2H), 7.24-7.19 (m, 3H), 4.20-4.07 (m, 2H), 3.57 (td, 2H, J = 11.5, 2.5 Hz), 2.80 (tt, 1H, J = 11.5, 4.2Hz), 1.94-1.75 (m, 4H), 1768-64-5
The synthetic route of 1768-64-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Article; Nuzzi, Andrea; Fiasella, Annalisa; Ortega, Jose Antonio; Pagliuca, Chiara; Ponzano, Stefano; Pizzirani, Daniela; Bertozzi, Sine Mandrup; Ottonello, Giuliana; Tarozzo, Glauco; Reggiani, Angelo; Bandiera, Tiziano; Bertozzi, Fabio; Piomelli, Daniele; European Journal of Medicinal Chemistry; vol. 111; (2016); p. 138 – 159;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics