Reference of 2695-48-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 2695-48-9 name is 8-Bromo-1-octene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
General procedure: Part of the solution of 8-bromo-1-octene (573.3 mg, 3.0 mmol) in THF (2 mL) was quickly addedvia syringe to a stirred solution of Mg (1.16 g, 5.0 mmol) and I2 (cat.) in THF (5 mL) under Aratmosphere. The mixture was heated until the color disappeared; then, the remaining 8-bromo-1-octene was added dropwise. After the addition was completed, the resulting reaction mixture washeated to reflux for 1 h and then was allowed to cool to room temperature. The prepared Grignardreagent was added slowly to a solution of D-arabino-nitrone (14) (417.5 mg, 1.0 mmol) in THF (10 mL)via syringe at 0 C under Ar atmosphere. The reaction mixture was stirred for 0.5 h; then sat. aq.NH4Cl was added to quench the reaction. The organic layer was separated and the aqueous layer wasextracted with EtOAc (3 ¡Á 20 mL). The combined organic phases were dried over MgSO4 and filtered;the solvent was removed under reduced pressure to give the crude product hydroxylamine 19, whichwas used without further purification because of its instability. The sample for structurecharacterization was purified by flash column chromatography on silica gel (petroleum ether/EtOAc= 5/1) as a colorless syrup.Data for (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2- ((benzyloxy)methyl)-1-hydroxyl-5-(oct-7-en-1-yl)pyrrolidine (19): [alpha]D 20 -8.6 (c 1.2 in CH2Cl2); numax/cm-1: 3030 (w), 2926 (s), 2855 (s), 1454 (m), 1362(w), 1097 (s), 735 (m), 697 (s); 1H-NMR (400 MHz, CDCl3) delta 7.32-7.24 (m, 15H), 5.80 (ddt, J = 16.9, 10.2,6.6 Hz, 1H), 5.01-4.91 (m, 2H), 4.56-4.42 (m, 6H), 3.95-3.92 (m, 1H), 3.80-3.76 (m, 2H), 3.58 (dd, J =9.2, 6.9 Hz, 1H), 3.54-3.50 (m, 1H), 3.17 (dt, J = 7.5, 5.4 Hz, 1H), 2.04-1.99 (m, 2H), 1.88-1.83 (m, 1H),1.50-1.43 (m, 1H), 1.42-1.28 (m, 8H); 13C-NMR (100 MHz, CDCl3) delta 139.3, 138.3, 138.2, 138.2, 128.5,128.5, 128.1, 128.0, 127.8, 127.8, 127.7, 114.3, 86.8, 84.7, 73.5, 71.8, 71.8, 70.2, 70.1, 68.4, 33.9, 29.8, 29.2,29.0, 26.7; HRMS(ESI) calcd for C34H44O4N+ [M + H]+ 530.32649, found 530.32565.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 8-Bromo-1-octene, and friends who are interested can also refer to it.
Reference:
Article; Wu, Qing-Kun; Kinami, Kyoko; Kato, Atsushi; Li, Yi-Xian; Jia, Yue-Mei; Fleet, George W.J.; Yu, Chu-Yi; Molecules; vol. 24; 20; (2019);,
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bromide – Wiktionary