Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 3718-04-5, name is 5-Vinyl-1H-imidazole, A new synthetic method of this compound is introduced below., SDS of cas: 3718-04-5
To a stirred solution of salen ligand (0.23 g, 0.9 mmol, 0.05 eq.) in i-PrOH (15 mL) was added MnCl2 (0.11 g, 0.9 mmol, 0.05 eq.) in anopened flask. After stirring with air bubbling at rt for 10 min, a solutionof SG1 nitroxide (5.09 g, 17 mmol, 1.0 eq.) and 4-vinyl-1H-imidazole 29(1.87 g, 20 mmol, 1.2 eq.) in i-PrOH (25 mL) was added, followed bysolid NaBH4 (0.75 g, 20 mmol, 1.2 eq.) added in small portions below25 C. The mixture was stirred at rt for 5.5 h, and the solvent was removedin vacuo. Then sat. NaHCO3 and CH2Cl2 were added and extractedwith CH2Cl2. The combined organic phase was washed withbrine, dried with MgSO4, and concentrated to afford a crude product asa 1: 1 mixture of diastereoisomers (31P-NMR ratio). The crude was separatedby flash column chromatography (CH2Cl2: MeOH=100: 0 to9: 1) to afford (RR/SS)-4a (1.29 g, 19%) and (RS/SR)-4a (1.38 g, 20%).(RR/SS)-4a: pale yellow solid; m.p.: 36-38 C; Rf=0.35 (CH2Cl2:MeOH=9: 1); 1H NMR (CDCl3, 400 MHz): delta 1.05 (s, 9H), 1.19 (t,J=7.1 Hz, 3H), 1.25 (s, 9H), 1.34 (t, J=7.1 Hz, 3H), 1.70 (d,J=6.6 Hz, 3H), 3.37 (d, J=27.4 Hz, 1H), 3.73-3.87 (m, 1H),3.93-4.07 (m, 2H), 4.07-4.20 (m, 1H), 5.13 (q, J=6.6 Hz, 1H), 6.91 (s,1H), 7.56 (s, 1H); 13C{1H}-NMR (CDCl3, 75 MHz): delta 16.0 (d,J=6.6 Hz), 16.2 (d, J=6.6 Hz), 20.2 (s), 27.5 (s), 30.5 (d, J=6.1 Hz),35.1 (d, J=4.4 Hz), 59.0 (d, J=7.2 Hz), 61.27 (d, J=6.0 Hz), 61.30(s), 69.5 (d, J=139.7 Hz), 73.7 (s), 121.2 (br. s), 134.6 (br. s), 136.2(br. s); 31P{1H}-NMR (CDCl3, 162 MHz): delta 26.45; HRMS (ESI-TOF) m/z:[M+H]+ Calcd for C18H37N3O4P 390.2516; Found 390.2514. (RS/SR)-4a: pale yellow solid; m.p.: 100-102 C; Rf=0.47 (CH2Cl2:MeOH=9: 1); 1H NMR (CDCl3, 400 MHz): delta 1.14 (s, 9H), 1.17 (s, 9H),1.20 (t, J=7.1 Hz, 3H), 1.36 (t, J=7.1 Hz, 3H), 1.62 (d, J=6.6 Hz,3H), 3.48 (d, J=27.9 Hz, 1H), 3.73-3.85 (m, 1H), 3.92-4.09 (m, 2H),4.09-4.21 (m, 1H), 5.11 (q, J=6.6 Hz, 1H), 7.01 (s, 1H), 7.54 (s, 1H);13C{1H}-NMR (CDCl3, 75 MHz): delta 15.9 (d, J=3.3 Hz), 16.0 (d,J=2.8 Hz), 17.6 (s), 27.8 (s), 30.7 (d, J=5.5 Hz), 35.0 (d, J=5.0 Hz),59.4 (d, J=7.7 Hz), 60.8 (s), 61.6 (d, J=6.6 Hz), 69.0 (d,J=138.6 Hz), 70.4 (s), 125.7 (br. s), 130.9 (br. s), 134.8 (s); 31P{1H}-NMR (CDCl3, 162 MHz): delta 27.59; HRMS (ESI-TOF) m/z: [M+H]+Calcd for C18H37N3O4P 390.2516; Found 390.2515.
The synthetic route of 3718-04-5 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Yamasaki, Toshihide; Buric, Duje; Chacon, Christine; Audran, Gerard; Braguer, Diane; Marque, Sylvain R.A.; Carre, Manon; Bremond, Paul; Bioorganic and Medicinal Chemistry; vol. 27; 10; (2019); p. 1942 – 1951;,
Imidazole – Wikipedia,
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