Electric Literature of 76469-88-0, A common heterocyclic compound, 76469-88-0, name is Methyl 4-(cyanomethyl)benzoate, molecular formula is C10H9NO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Step 1; Methyl 4-(cyanomethyl)benzoate (1.8 g, 10 mmol, 1 eq) was dissolved in THF (100 mL) and cooled to 0C. Sodium hydride (60% w/w in mineral oil, 820 mg, 20 mmol, 2 eq) was added portionwise and the mixture was stirred for 10 minutes. Methyl iodide (1.3 mL, 20 mmol, 2 eq) was added dropwise and the reaction was stirred at 0C until the starting material was consumed by TLC (2 hours). The reaction mixture was quenched with water and was partitioned between EtOAc and brine. The aqueous layer was discarded, and the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and evaporated to afford a crude residue which was chromatographed on silica gel (gradient elution, 0% to 50% EtOAc in hexanes, Si02) to afford the desired product as a white crystalline solid (1.88g, 74%).
The synthetic route of 76469-88-0 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SCHERING CORPORATION; WONG, Michael, K.; LAVEY, Brian, J.; YU, Wensheng; KOZLOWSKI, Josheph, A.; DEMONG, Duane, E.; DAI, Xing; STAMFORD, Andrew, W.; MILLER, Michael, W.; ZHOU, Guowei; YANG, De-Yi; GREENLEE, William, J.; WO2011/119559; (2011); A1;,
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