Electric Literature of 1528-41-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1528-41-2, name is Ethyl 2-(4-cyanophenyl)acetate belongs to nitriles-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
A mixture of 1.0 g of 3,3-dimethylcyclohexanone (S6; 7.9 mmol), hydroxylamine hydrochloride (0.66 g,9.5 mmol), 10 mL of ethanol, and 1.6 g of K2CO3 (12 mmol) was heated to 70 C for 64 hours. Themixture was concentrated suspended in 10 mL of water, the extracted three times each with 30 mL ofEtOAc. The extracts were combined and concentrated to provide 1.2 g of 3,3-dimethylcyclohexanoneoxime (S7) that was used crude. To a 0 C solution of S7 (0.20 g, 1.4 mmol) in 2 mL of THF was added dropwise 1.6 M BuLi in hexanes(1.8 mL, 2.8 mmol). The mixture stirred for 30 minutes at room temperature, then ethyl 2-(4-cyanophenyl)acetate (0.27 g, 1.4 mmol) was added. After stirring for 1 hour, 0.7 mL of concentratedH2SO4 was added. After stirring for 1 hour, 25 mL of water was added and the mixture was extractedthree times each with 15 mL of EtOAc. The extracts were concentrated and the residue was purified firstby silica chromatography (0-50% EtOAc in heptanes), then by preparative HPLC (C18 column 10-90%MeCN in H2O, both 0.1% v/v formic acid) or give 41 mg of 16.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-(4-cyanophenyl)acetate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Meyers, Kenneth; Cogan, Derek A.; Burke, Jennifer; Arenas, Raquel; Balestra, Michael; Brown, Nicholas F.; Chen, Zhidong; Cerny, Matthew A.; Clifford, Holly E.; Colombo, Federico; Fader, Lee; Frederick, Kosea S.; Guo, Xin; Goldberg, Daniel; Hornberger, Keith R.; Kugler, Stanley; Lord, John; Marshall, Daniel R.; Moss, Neil; Parmentier, Jean-Huges; Richman, Jeremy R.; Schmenk, Jennifer; Weldon, Steven M.; Yu, Maolin; Zhang, Michael; Bioorganic and Medicinal Chemistry Letters; vol. 28; 5; (2018); p. 979 – 984;,
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