Reference of 874-97-5, 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. 874-97-5 name is 3-Cyanobenzyl alcohol, 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.
3-Cyanobenzyl alcohol (308 mg, 2.32 mmol), N-hydroxyphthalimide (416 mg, 2.55 mmol) and triphenylphosphine (668 mg, 2.55 mmol) were dissolved in THF (8 mL). Diethyl azodicarboxylate (DEAD) (0.40 mL, 2.55 mmol) was added dropwise while stirring to the solution and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was filtered and the residue washed with THF (4 mL) and dried under high vacuum. The crude product (1.24 g, 4.46 mmol) was dissolved in ethanol (8 mL) and hydrazine monohydrate (0.43 mL, 8.92 mmol) was added. The reaction was refluxed for 2 h and filtered. Ethanol was removed under reduced pressure and the residue suspended in ethyl ether. The ethyl ether layer was washed with 3% Na2CO3 (2*10 mL), brine (10 mL) and concentrated. The crude product (830 mg, 5.61 mmol) was dissolved in THF (15 mL) and cooled to 0 C. Lithium aluminum hydride (1 M in THF, 11.2 mL, 11.2 mmol) was added dropwise and the reaction was stirred overnight at room temperature. It was then quenched with methanol (10 mL) and water (2 mL). The mixture for stirred for a further 30 min. The salts were filtered off and the solvent removed by evaporation in vacuo. The crude product was purified by silica gel flash column chromatography using 20% MeOH/dichloromethane as eluent to afford the desired product as white solid (59 mg, 0.388 mmol, 17% over 3 steps). 1H NMR (CDCl3, 300 MHz): delta (ppm) 4.07 (s, 2H), 4.63 (s, 2H), 5.18 (s, 4H), 7.36-7.44 (m, 4H).
At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Cyanobenzyl alcohol, and friends who are interested can also refer to it.
Reference:
Patent; NEWLINK GENETICS CORPORATION; Mautino, Mario; Jaipuri, Firoz; Marcinowicz-Flick, Agnieszka; Kesharwani, Tanay; Waldo, Jesse; (201 pag.)US10047066; (2018); B2;,
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