Reference of 15963-46-9, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 15963-46-9, name is Methyl 3-chlorocyclobutanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.
5-(2,4-dichlorophenyl)-1,3,4-oxadiazole-2-thiol (0.1 g, 0.41 mmol), cesium carbonate (0.17 g, 0.51 mmol), and sodium iodide (0.006 g, 0.04 mmol) were dissolved in 2 mL DMSO. Methyl 3-chlorocyclobutanecarboxylate (0.09 g, 0.61 mmol, 0.08 mL) was added and the mixture was stirred at 100 C. for 40 hr. The reaction was diluted with EtOAc and H2O, and product was extracted with EtOAc (3*15 mL). The organic layers were combined, washed with brine (2*15 mL), and evaporated in vacuo. The oil was subjected to silica gel chromatography eluting with 15% EtOAc: 75% Hex. The diastereomers were separated and fractions containing products were concentrated. Trans: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.91 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.48-4.38 (m, 1H) 3.73 (s, 3H) 3.40 (tt, J=10.4, 5.7 Hz, 1H) 2.94 (tt, J=8.4, 5.8 Hz, 2H) 2.56 (dtd, J=13.3, 6.4, 2.4 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 174.87, 164.01, 163.34, 138.08, 133.74, 131.58, 131.19, 127.61, 121.39, 52.07, 37.62, 35.22, 32.73; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 8.02 min. cis: 1H NMR (500 MHz, CDCl3-d) delta ppm 7.90 (d, J=8.5 Hz, 1H) 7.57 (d, J=2.0 Hz, 1H) 7.39 (dd, J=8.5, 2.0 Hz, 1H) 4.30 (p, J=8.6 Hz, 1H) 3.71 (s, 3H) 3.17 (p=8.9 Hz, 1H) 2.95-2.85 (m, 2H) 2.55 (qd, J=9.7, 2.9 Hz, 2H); 13C NMR (500 MHz, CDCl3-d) delta ppm 173.80, 164.17, 163.30, 138.03, 133.72, 131.57, 131.16, 127.59, 121.39, 52.02, 35.45, 34.45, 33.77; TOF ES+ MS: (M+H) 359.0; HPLC Ret: 7.89 min.
The chemical industry reduces the impact on the environment during synthesis Methyl 3-chlorocyclobutanecarboxylate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF MICHIGAN; BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY; Larsen, Scott D.; Neubig, Richard; Hutchings, Kim; Kahl, Dylan; Lisabeth, Erika Mathes; (56 pag.)US2019/308947; (2019); A1;,
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