Electric Literature of 1885-38-7, A common heterocyclic compound, 1885-38-7, name is (E)-Cinnamonitrile, molecular formula is C9H7N, 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.
General procedure: To a mixture of dimethyl-3-p-tolyloxiranyl-2,2-dicarboxylate(1a, 0. 25 g, 1 mmol, 1 equiv) and benzonitrile (2a, 0.52g, 5mmol, 5 equiv) was added SnCl4 (0.12 mL, 1 mmol, 1 equiv) at 0C. The reaction mixture was then stirred at r.t. until the startingmaterials were consumed as indicated by TLC analysis. Themixture was poured into 50 mL aq sat. NaHCO3 solution andextracted with CH2Cl2 (3 × 25 mL). The combined organic layerwas rinsed with H2O, brine, and dried over anhydrous MgSO4.The solvent was evaporated off to get a residue which was thenpurified by flash chromatography to give pure product 3aa (269mg, 76%). 1H NMR (500 MHz, CDCl3): delta = 8.11 (d, J = 7.8 Hz, 2 H),7.54 (t, J = 7.5 Hz, 1 H), 7.46 (t, J = 7.5 Hz, 2 H), 7.19 (d, J = 7.9 Hz,2 H), 7.11 (d, J = 7.9 Hz, 2 H), 6.15 (s, 1 H), 3.90 (s, 3 H), 3.20 (s, 3H), 2.31 (s, 3 H). 13C NMR (125 MHz, CDCl3): delta = 167.6, 166.0,162.9, 138.2, 133.5, 132.2, 128.9, 128.9, 128.6, 128.0, 126.6,90.7, 76.6, 53.8, 52.5, 21.3. HRMS: m/z calcd for C20H19NO5 [M +H+]: 354.1336; found: 354.13302
The synthetic route of 1885-38-7 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Zhou, Hai; Zeng, Xiaofei; Xie, Yan; Zhong, Guofu; Synlett; vol. 26; 12; (2015); p. 1693 – 1696;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts