1,2-Dimethoxyethane, as solvent

The submitters have found that diglyme and 1,2-dimethoxyethane are also effective solvents. The reactivity of the magnesium obtained with 1,2-dimethoxyethane as solvent is slightly reduced. Hydrocarbons, amines, and dioxane proved to be ineffective solvents owing to the insolubility of the magnesium salts and consequent incomplete reduction. 

With long alkyl chain alcohols, the conversion of fructose with 1-octanol to octylfructosides was only 60%, but with 1-decanol and 1-dodecanol the conversion dropped to 40% due to competing of fructose ring opening. However, in 1,2-dimethoxyethane as solvent, a yield in dodecyl-D-fructosides of 60% was obtained after 1.5 h at 83 °C. 

The checkers obtained no product using tetrahydrofuran as the solvent. In accordance with a suggestion by J. C. Marchon,8 they substituted 1,2-dimethoxyethane as solvent and achieved iron insertion in four (4) hours with a 50% yield. 

The reaction of ketones with dialkylaminosulfur trifluorides gives gcw-difluoro compounds (see VoI.ElOa, pp414-416. and reft 30 and 31), however, in some cases minor amounts of monofluoroalkenes are formed as byproducts. By using 1,2-dimethoxyethane as solvent monofluoroalkenes have been synthesized in fair to good yields. "... 

When iodine, bromine or (V-bromosuccinimide is utilized as the source of the electrophile, the optimized conditions are water in 1,2-dimethoxyethane as solvent, at 20 °C. Thus, N.N-2-trimethyl-4-pentenethioamide (9, R = CH,) was cyclized to give the corresponding iodolactone 11 (R = CH3 X = I) in 42% yield and 91 9 selectivity. 

The procedure is described in dimethoxyethane as solvent similar experimental conditions are used in THF. 

In the original procedure Wadsworth and Emmons used sodium hydride as base and 1,2-dimethoxyethane as solvent. In a Japanese procedure sodium amide is used as base and tetrahydrofurane as solvent. The reagent reacts with steroids having a keto group at C3, Cn, or Cio and is thus less selective than triethylphosphonoacetate,... 

Amino-3-cyano-4,5-dihydrofurans (299) are prepared from oxiranes and sodium malonodinitrile,167-169 and the corresponding dihydrothiophenes (300) are similarly obtained by treatment of thiirane with sodium malonodi-nitrile. But the procedures reported170 had to be modified considerably a temperature of — 20°C and dimethoxyethane as solvent gave better yields169 (Scheme 82). Attempts to transfer this synthesis to iV-tosylaziridine (301),... 

Standard oxidative coupling methods for acetylenes use the Glaser method (CuCl, NH4CI, aqueous alcohol, O2) or Eglinton and Galbraith s method [Cu(OAc)a, pyridine, alcohol]. The former reaction can be accelerated by addition of JYiV A -tetramethylethylenediamine and the yield improved by using dimethoxyethane as solvent. ... 

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