Application of 1885-38-7, 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. 1885-38-7 name is (E)-Cinnamonitrile, 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: In a Schlenck flask filled with gaseous carbon dioxide, to a stirred THF (1.5 mL) solution of the alpha,beta-unsaturated compound 1 (0.25 mmol) and bis(acetylacetonato)cobalt(II) (conditions A: 3.2 mg, 5 mol %; conditions B: 6.4 mg, 10 mol %) was added a 1.0 M n-hexane solution of diethylzinc (conditions A: 0.5 mL, 2 equiv; conditions B: 1.0 mL, 4 equiv) at 0 C, then the reaction mixture was stirred at 20 C for 1-48 h. After checking the completed reaction by TLC analysis, the reaction mixture was quenched with a 1.0M hydrochloric acid diethyl ether solution (conditions A: 1.5 mL, 6 equiv; conditions B: 3.0 mL, 12 equiv) at 0 C. The organic layer was extracted with diethyl ether, washed with brine, dried over sodium sulfate and concentrated in vacuum. The residue was purified by silica gel column chromatography (Hexanes:AcOEt:HCOOH = 1:1:0.003) to afford the desired carboxylic acid 2. The resulting compound was diluted with a mixed solution (6.25 mL, diethyl ether:MeOH = 5:1) and methylated with trimethylsilyldiazomethane in n-hexane (ca. 0.6M solution, (1.04 mL, 2.5 equiv)). After purification by chromatography on silica gel, the corresponding methyl carboxylate was isolated.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Cinnamonitrile, and friends who are interested can also refer to it.
Reference:
Article; Hayashi, Chika; Hayashi, Takuo; Yamada, Tohru; Bulletin of the Chemical Society of Japan; vol. 88; 6; (2015); p. 862 – 870;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts