Triglyme ether

Tms (trimethylsilyl) = MejSi triglyme triethylene glycol dimethyl ether =... 

Triethylene glycol dimethyl ether (triglyme) [112-49-2] 1.425. Refluxed with, and distd from sodium hydride or LiAlH4. 

Compounds which produce a complex with Li+ ions have been investigated. The compounds examined were N,N,N, N tetramethylethylenediamine (TMEDA), eth-ylenediamine, crown ethers, cryptand [211], diglyme, triglyme, tetraglyme, eth-ylenediamine tetraacetic acid (EDTA) and EDTA-Li+ (n=l, 2, 3) complexes [59]. The cycling efficiency was improved by adding TMEDA, but the other additives did not show distinct effects. 

To the flask containing the crude product, add 2.0 g (0.02 mol) of maleic anhydride and 25 ml of triethyleneglycol dimethyl ether ( triglyme , b.p. 222 °C), fit a reflux condenser and boil under reflux for 10 minutes over a Bunsen flame. Cool the solution to about 100°C, add 10ml of 95 per cent ethanol and pour into a solution of 3.0 g of sodium hydroxide in 75 ml of water. Stir for a few minutes, then cool in ice-water and filter under suction. Wash the residue with chilled methanol/water (4 1 v/v) and recrystallise from methylcyclohexane or a chloroform/methanol mixture to give colourless plates of 9-bromotriptycene, m.p. 251-256 °C yield is 1.5 g (45%). Further recrystallisation gives the pure product, m.p. 258-262 °C. 

The same results were obtained in THF, ether, DME or in the presence of TMEDA, triglyme, HMPA or crown ethers. 

The complexes are very soluble in methanol, ethanol, butanol, methyl Cellosolve (2-methoxyethanol), and ethyl Cellosolve (2-ethoxyethanol), and to a fair degree, quite soluble in 1,2-dimethoxyethane and di- and triglyme. They are initially quite soluble in tetrahydrofuran, acetone, pyridine, nitro-methane, acetonitrile, dimethyl sulfoxide, and iV,A/-dimethyl-formamide, but usually precipitation of the nickel halide-solvent complex occurs if attempts are made to prepare moderately concentrated solutions in these solvents. They are only very slightly soluble, or are quite insoluble in dioxane, ethyl ether, hexane, dichloromethane, ethyl acetate, and methyl- and butyl-cellosolve acetate (2-methoxyethyl and 2-butoxyethyl acetate). 

In order to study the factors determining the regioselectivity of sodium borohydride reduction of a, -unsaturated ketones, reactions with 3-methylcyclohexenone, carvone and cholestenone were carried out in 2-propanol, diglyme, triglyme or pyridine. Mixtures of 1,2- and 1,4-reduction products were obtained in the alcoholic and ether solvents, whereas pure 1,4-reduction was observed in pyridine. Addition of triethylamine to NaBH4 in diglyme led to formation of triethylamine borine, EtsN BHs. Similarly, with pyridine, pyridine borine could be isolated, leading to exclusive 1,4-reductions. 

Place 1.5 g of , -1,4-diphenyl-1,3-butadiene (from the Wittig reaction. Chapter 34) and 1.0 mL (1.1 g) of dimethyl acetylenedicarboxylate caution, skin irritant ) in a 25 x 150-mm test tube and rinse down the walls with 5 mL of triethylene glycol dimethyl ether (triglyme) (bp 222°C). Clamp the test tube in a vertical position, introduce a cold finger condenser, and reflux the mixture gently for 30 min. Alternatively, carry out the experiment in a 25-mL round-bottomed flask equipped with a reflux condenser. Cool the yellowish solution under the tap, pour into a separatory funnel, and rinse out the reaction vessel with a total of about 50 mL of ether. Extract twice with water (50-75 mL portions) to remove the high-boiling solvent, shake the ethereal solution with saturated sodium chloride solution, and dry the ether layer over anhydrous sodium sulfate. Filter or decant the ether solution into a tared 125-mL Erlenmeyer flask and evaporate the... 

CH3OCH2CH2OCH2 Triethylene glycol dimethyl ether (triglyme) Miscible with water... 

Collect the solid on a small Buchner funnel and wash it with the chilled solvent to remove brown mother liquor. Transfer the moist, nearly colorless solid to a tared 125-mL round-bottomed flask and evacuate on the steam bath until the weight is constant the anthracene-triptycene mixture (mpabout 190-230°C) weighs 2.1 g.Addl gofmaleic anhydride and 20 mL of triethylene glycol dimethyl ether ( triglyme, bp 222°C), heat the... 

The Hammond Co. supplies an indicating form which turns from blue to red when exhausted. It is prepared by impregnating the surface of the calcium sulfate granules with 3.5-5% of anhydrous cobalt chloride. The blue cobalt salt is indifferent to aprotic solvents insoluble in water (benzene) or partially soluble in water (diethyl ether), but is leached off by water-miscible solvents, both protonic (ethanol, acetic acid) tmd aprotic (dimethylformamide, dimethyl sulfoxide, triglyme). 

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