Electric Literature of 627-42-9, These common heterocyclic compound, 627-42-9, name is 2-Methoxyethyl chloride, 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.
An excess of n-BuLi (2.5 M in n-hexane; 1.0 mL, correct stoichiometric amount corresponding to 0.50 mL, 1.24 mmol) was added via cannula through a rubber septum to a flask containing N,N-bis(2-phosphinoethyl)methoxyethylamine (5′) (60 mg, 0.31 mmol) in freshly distilled THF (10 mL) at 0 C. The solution became dark (black-violet coloured). Still at 0 C., under stirring, 2-chloroethyl methylether (236 mg, 2.48 mmol) dissolved in distilled THF (5 mL) was added dropwise. The mixture was left to reach room temperature overnight becoming yellow-gold coloured. It was then reduced to one third of the initial volume by a gentle stream of dinitrogen. Distilled diethylether (20 mL) was added. The flask was cooled again with an ice bath and degassed water (5 mL) was added dropwise. Two phases were formed: the upper organic phase was yellow-gold coloured, whereas the aqueous phase was almost colourless. Degassed diethylether (20 mL) was added, and the mixture was transferred in a separatory funnel (previously fluxed with dinitrogen) via cannula to avoid the contact with the atmosphere. Always under a dinitrogen atmosphere the lower aqueous phase was recovered in another separatory funnel and treated with additional diethylether (2×10 mL). Then the aqueous phase was discharged and the combined ethereal phases were placed in a 100 mL round bottom flask containing anhydrous Na2SO4 (ca. 500 mg). The solid was filtered off under dinitrogen and washed with additional anhydrous diethylether (2×10 ml). The combined ethereal phases were concentrated under dinitrogen and then under vacuum (yield ca. 60%).1H NMR (CDCl3): delta(ppm)=3.57-3.47 (10H); 3.33 (s, 12H); 3.32 (s, 3H); 2.66 (m, 6H); 1.78 (t, 8H); 1.65 (m, 4H).13C NMR (CDCl3): delta(ppm)=71.02 (s); 70.39 (d); 58.86 (s); 52.48 (s); 52.52 (s); 50.83 (d); 27.96 (d); 24.75 (d).31P{1H} (CDCl3): delta(ppm)=-39.0.
The synthetic route of 627-42-9 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; NIHON MED-PHYSICS CO., LTD.; US2010/160615; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics