Synthetic Route of 3469-00-9,Some common heterocyclic compound, 3469-00-9, name is Methyl Diphenylacetate, molecular formula is C15H14O2, 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.
A 2.5 M solution of n-BuLi in hexane (2.04 mL, 5.10 mmol, 1.02 equiv) is added dropwise to a solution of diisopropylamine (0.74 mL, 5.25 mmol,1.05 equiv) in anhydrous THF (5 mL) at -78 C under Ar atmosphere and thereaction mixture is allowed to stir for 30 min at -78 C. After stirring an additional 30 min at -5 C, a solution of methyl 2,2-diphenylacetate (1.13 g, 5.00 mmol,1.00 equiv) in anhydrous THF (2 mL) is added dropwise at -78 C, and the reaction mixture is allowed to stir for 10 min. Finally, crotyl bromide (trans, 85% pure; 810 mg,6.00 mmol, 1.20 equiv) is added dropwise at -78 C and the mixture is slowly warmed to rt. After stirring for 16 h at rt, the reaction mixture is cooled to 0 C, quenched by the addition of saturated aq. NH4Cl (10 mL) then extracted with Et2O (4 × 10 mL). The combined organic extracts are washed with brine, dried overanhydrous Na2SO4, filtered and concentrated under reduced pressure; yield: 1.00 g, 3.57 mmol, 71%, yellow liquid. The product is obtained as inseparable mixture of E/Z isomers (90:10; cf. NMR spectra).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl Diphenylacetate, its application will become more common.
Reference:
Article; Rode, Katharina; Palomba, Martina; Ortgies, Stefan; Rieger, Rene; Breder, Alexander; Synthesis; vol. 50; 19; (2018); p. 3875 – 3885;,
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