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 mixed solution of 62 (7.25 g, 32.5 mmol) and L12CUCI4 (16.2 mL, 0.1 M solution in THF, 1.62 mmol, 5 mol %) in THF (50 mL) at 0C was slowly added Grignard reagent ((cyclobutylmethyl)magnesium bromide) that5 was made from (bromomethyl)cyclobutane (9.69 g, 65.0 mmol) and grinded magnesium turnings (3.16 g, 130 mmol) in Et20 (50 mL). After the addition completed, stirred at 0C for 30 min and then at RT for 18 hr. The reaction was quenched by NH4Cl at 0C and stirred at RT for 20 min. Then the mixture was treated with hexanes and water. Organic phase was washed by brine, dried over Na2S04, and concentrated to give 63 (6.9 g, 100%) as a colorless oil. ‘H NMR (400 MHz, Chloroform-ri) d 4.57 (dd, J= 4.5, 2.7 Hz, 1H), 3.87 (ddd, .7= 11.1, 7.4, 3.4 Hz, 1H), 3.72 (dt, J = 9.6, 6.9 Hz, 1H), 3.56 – 3.45 (m, 1H), 3.37 (dt, J= 9.6, 6.7 Hz, 1H), 2.24 (dq, J= 15.5, 7.8 Hz, 1H), 2.10 – 1.93 (m,3H), 1.91 – 1.64 (m, 4H), 1.62 – 1.45 (m, 7H), 1.39 (q, J= 7.4 Hz, 2H), 1.25 (tdd, J= 10.0, 7.2, 3.9 Hz, 2H). 13C NMR (101 MHz, Chloroform-ri) d 98.78, 67.65, 62.28,36.79, 36.06, 30.73, 29.70, 28.32 (2C), 25.46, 23.77, 19.66, 18.43.
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; TSRL, INC.; LIPKA, Elke D.; SIMON, Eric; WHITE, Andy, D.; HUTCHINGS, Kim, M.; GAN, Xinmin; (0 pag.)WO2020/6050; (2020); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics