Extracurricular laboratory: Synthetic route of tert-Butyl methyl malonate

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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., COA of Formula: C8H14O4

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. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., COA of Formula: C8H14O4

A 100 mL round-bottom flask equipped with a stirring bar was charged with compound 7 (1000 mg, 5.8 mmol) and DMF (20 mL). To the solution, sodium hydride (60percent oil suspension, 233 mg, 5.8 mmol) was added. The reaction was allowed to stir at 0 °C for 1 h. To the mixture, 4-bromobenzyl bromide (1437 mg, 5.8 mmol) was added at 0 °C and the mixture was stirred at room temperature for 20 h. To the reaction mixture, H2O was added, and the mixture was extracted with CH2Cl2 (3x), dried over MgSO4, and concentrated in vacuo. The remaining residue was purified by silica gel column chromatography (hexanes/AcOEt = 90:10) to afford the desired product 4 (1551 mg, 79percent) as a colorless oil. 1H NMR (400 MHz, CDCl3) delta 7.39 (d, J = 8.3 Hz, 2H), 7.08 (d, J = 8.3 Hz, 2H), 3.70 (s, 3H), 3.53 (t, J = 7.8 Hz, 1H), 3.13 (d, J = 7.8 Hz, 2H), 1.40 (s, 9H); 13C NMR (100 MHz, CDCl3) delta 169.4, 167.5, 137.0, 131.5, 130.6, 120.5, 83.2, 54.3, 52.4, 34.0, 27.8; HR-FAB MS calcd for C15H20BrO4 [M+H]+ 343.0545, found 343.0558.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Kanemitsu, Takuya; Furukoshi, Saeka; Miyazaki, Michiko; Nagata, Kazuhiro; Itoh, Takashi; Tetrahedron Asymmetry; vol. 26; 4; (2015); p. 214 – 218;,
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