Electric Literature of 16545-68-9 ,Some common heterocyclic compound, 16545-68-9, molecular formula is C3H6O, 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.
At 0C and under nitrogen flux, NaH (60% dispersion in mineral oil) (0.510 g; 12.8 mmol) was added portionwise to a solution of cyclopropanol (0.64 mL, 12.74 mmol) in Me-THF (24mL). The reaction was stirred at room temperature for 10 minutes. (1844) At -78C, the above described suspension was added dropwise to a solution of 1,4- dinitro-lH-pyrazole (3.00 g; 18.98 mmol) in Me-THF (6.50 mL, 64.9 mmol). The reaction mixture was stirred at -78C for 1 h then allowed to stir at rt for 5 hours. The reaction mixture was poured out onto water, made acidic with 3N HCl(aq), extracted with DCM, dried over MgS04, filtered and evaporated. The crude was purified via preparative LC (Stationary phase irregular SiOH 15-40muiotaeta 24g GraceResolv, Mobile phase: gradient from 80% Heptane, 20% EtOAc to 40% heptane, 60% EtOAc). The pure fractions were collected and the solvent was evaporated to give 466 mg of intermediate 746 (22%).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,16545-68-9, its application will become more common.
Reference:
Patent; JANSSEN PHARMACEUTICA NV; STANSFIELD, Ian; QUEROLLE, Olivier, Alexis, Georges; LIGNY, Yannick, Aime, Eddy; GROSS, Gerhard, Max; JACOBY, Edgar; MEERPOEL, Lieven; GREEN, Simon, Richard; HYND, George; KULAGOWSKI, Janusz, Jozef; MACLEOD, Calum; MANN, Samuel, Edward; (472 pag.)WO2018/2217; (2018); A1;,
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