Some common heterocyclic compound, 4341-76-8, name is Ethyl 2-butynoate, molecular formula is C6H8O2, 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. category: esters-buliding-blocks
To a solution of CuI (1.8 g, 9.6 mmol) and TMEDA (3.6 mL, 24 mmol) in THF (1.0 mL) was added 2-phenylethylmagnesium bromide (0.7 M in THF, 13.7 mL, 9.6 mmol) at -40 C, and the resulting mixture was stirred at -40 C for 30 min. To the mixture was added ethyl 2-butynoate (0.9 g, 8 mmol) at -78 C, and the mixture was stirred at -78 C for 2 h. Saturated NH4Cl aq was added and the mixture was allowed to warm to rt. The resulting slurry was diluted with EtOAc (50 mL) and washed with H2O and brine. The organic layer was separated and dried over MgSO4. Then, the drying agent was removed by filtration, and the resulting solution was evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (0-10% EtOAc/hexane) provided ethyl (E)-3-methyl-5-phenyl-2-pentenoate (1.7 g, 7.6 mmol) in 95% yield.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4341-76-8, its application will become more common.
Reference:
Article; Hojoh, Kentaro; Shido, Yoshinori; Nagao, Kazunori; Mori, Seiji; Ohmiya, Hirohisa; Sawamura, Masaya; Tetrahedron; vol. 71; 37; (2015); p. 6519 – 6533;,
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