583-02-8, name is Ethyl 4-(trifluoromethyl)benzoate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: esters-buliding-blocks
General procedure: To a solution of 1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl iodide (0.22 mL, 1.0 mmol), ethyl benzoate (0.16 mL, 1.1 mmol) in Et2O (3 mL) was added at -80C methyllithium (1.5 M in Et2O with lithium bromide; 0.73 mL, 1.1 mmol) and stirring was continued for 30 min at the same temperature where diethyl-aluminium chloride (1 M in n-hexane; 1.1 mL, 1.1 mmol) was gradually added and further stirring for 15 min at -80 C. In a separate flask, lithium bromide (0.12 g, 1.4 mmol), triethyl phosphonoacetate (0.26 mL, 1.3 mmol), and THF (1 mL) was mixed at 0 C where triethylamine (0.19 mL, 1.4 mmol) was added and the solution was stirred for 10 min at room temperature. This mixture was slowly introduced to an aluminium acetal solution prepared above with the aid of cannula and the whole mixture was further stirred for 1 h at room temperature. To this solution were successively added Et2O (3 mL), NaF (0.185 g, 4.4 mmol) and H2O (59 mg, 3.3 mmol), which was stirred for 0.5 h at room temperature. Filtration with a pad of silica gel and concentration furnished a crude mixture which was purified by silica gel column chromatography (n-hexane:CH2Cl2=6:1) to afford 0.484 g (0.979 mmol, 98% yield, E_Z=>99:1) of the title compound 5ca as a colourless oil.
The synthetic route of 583-02-8 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Yamazaki, Takashi; Mano, Noriko; Hikage, Reo; Kaneko, Tsutomu; Kawasaki-Takasuka, Tomoko; Yamada, Shigeyuki; Tetrahedron; vol. 71; 42; (2015); p. 8059 – 8066;,
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