Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 33143-29-2, name is 2,2-Dimethyl-2H-chromene-6-carbonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C12H11NO
To a stirred solution of 1 (0.8 g, 4.3 mmol), NMO (2.9 g, 21.6 mmol) and (S,S)-Jacobsen catalyst (0.06 g, 0.10 mmol) in CH2Cl2 (30 mL) was added m-CPBA (1.5 g, 8.6 mmol) over 30 min at 0 C under N2 atmosphere. The resulting mixture was stirred for 4 h at room temperature. The reaction mixture was diluted with Et2O (50 mL), and quenched with 5% H2SO4 in H2O (7.5 mL). The aqueous phase was extracted with EtOAc (30 mL x 3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (n-hexane/EtOAc = 6:1) to afford 11 0.82g (4.1 mmol, 94%) as white solid. Rf = 0.60 (n-hexane/EtOAc = 3:1); mp = 142-144 oC; [alpha]D25 = -97.9 (c 0.1, MeOH); IR (neat) nu 2980, 2226, 1615, 1579, 1490, 1466, 1371, 1347, 1279, 1238, 1209, 1155, 1131, 1106, 1045, 955, 911, 866, 808 cm-1; 1H NMR (400 MHz, CDCl3) delta 7.66 (d, J = 2.0 Hz, 1H), 7.53 (dd, J = 8.5, 2.0 Hz, 1H), 6.87 (d, J = 8.5 Hz, 1H), 3.92 (d, J = 4.3 Hz, 1H), 3.54 (d, J = 4.4 Hz, 1H), 1.60 (s, 3H), 1.30 (s, 3H); 13C NMR (100 MHz, CDCl3) delta 156.5, 134.4, 133.8, 121.1, 119.0, 118.7, 104.3, 74.6, 62.3, 49.9, 25.5, 23.0; HRMS (ESI) calcd for C12H12NO2 [M+H]+ 202.0867, found 202.0861; HPLC (Daicel OD-RH column, n-Hexane:Isopropylalcohol = 95:5, 0.5 ml/min, 254nm) Rt (major) = 18.19 min, Rt (minor) = 20.00; ee = 91%.
The synthetic route of 33143-29-2 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Ma, Sang-Ho; Kim, Yeon Su; Jung, Jun Min; Boggu, Pulla Reddy; Kim, Seung Chan; Kim, In Su; Jung, Young Hoon; Tetrahedron Letters; vol. 61; 5; (2020);,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts