2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, its 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.
To a suspension of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) in DMF (5 mL) was added a solution of 2-(2-(benzyloxy)ethoxy)ethanol (commercially available from for example Aldrich) (2.74 mL, 15.29 mmol) in DMF (5 mL) at 0 C. After stirring for 25 min, 1,4-dibromobutane (commercially available from for example Aldrich) (14.9 g, 68.8 mmol) dissolved in DMF (5 mL) was added dropwise to the mixture. The reaction was warmed to ambient temperature and stirred under an atmosphere of nitrogen for 2.5 hours. A further aliquot of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) was added and the reaction was stirred at 0 C. for 30 minutes and at ambient temperature for 30 minutes. A final aliquot of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) was added and the reaction stirred at ambient temperature for 2 hours then left standing overnight. The reaction mixture was filtered through celite and the solid washed with DCM. The filtrate was partitioned between DCM (30 mL) and water (30 mL). The organic extract was washed with brine (2¡Á30 mL), dried using a hydrophobic frit, and concentrated under reduced pressure. The product was purified by chromatography on silica using a using a gradient elution from 0% to 80% methyl tert-butyl ether in cyclohexane to afford the title compound (3 g, 9.06 mmol, 59% yield). LCMS RT=1.19 min, ES+ve m/z 331.2/333.2 [M+H]+.
According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Crews, Craig M.; Buckley, Dennis; Ciulli, Alessio; Jorgensen, William; Gareiss, Peter C.; Van Molle, Inge; Gustafson, Jeffrey; Tae, Hyun-Seop; Michel, Julien; Hoyer, Dentin Wade; Roth, Anke G.; Harling, John David; Smith, Ian Edward David; Miah, Afjal Hussain; Campos, Sebastien Andre; Le, Joelle; US2014/356322; (2014); A1;,
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