2- ethyl sodium

A. Ethyl Sodium Phthalimidoinalonate.—To a solution of 9.2 g. (0.4 gram atom) of sodium in 300 cc. of absolute alcohol at 60° is added, with efficient stirring, 126 g. (0.41 mole) of ethyl phthalimidomalonate (Org. Syn. Coll. Vol. i, 266). The mixture is rapidly chilled to 0° and the crystalline product filtered at once by suction and washed successively with two 200-cc. portions of absolute alcohol and two 200-cc. portions of ether. After first drying in a vacuum desiccator and then heating for eight hours imder 15 mm. pressure in a flask suspended in an oil bath at 145-155° (Note i), it weighs 108-III g. (82-85 per cent of the theoretical amount). 

B. Ethyl I -Methyllhiol- -phthalimidopropane-, 3 -dicarboxylate. —A mixture of 85 g. (0.26 mole) of ethyl sodium phthalimidomalonate and 43 g. (0.39 mole) of, fl-chloroethyl methyl sulfide (p. 18) is heated in an oil bath at 160-165° in a i-l. three-necked flask, fitted with a condenser, a thermometer, and a stoppered... 

The ethyl sodium phthalimidomalonate crystallizes with 1.5 molecules of alcohol, which is removed only on heating above 140° in vacuo. 

Thiophene is also metal ated by a benzene-soluble ethyl sodium-diethyl zinc complex. Upon carbonation, 65% of 2-thiophenecar-boxylic acid was obtained. ... 

Ethyl pentadecylate, 16, 37 Ethyl pentanehexacarboxylate, 10, 59 Ethyl phenylacetate, 16, 33 Ethyl -phenylacetoacetate, 18, 36 Ethyl -y-phenylbctyrate, 18, 25, 26 Ethyl phenylcyanopyruvate, 11, 40 Ethyl /J-phenylethyl ketone, 16, 49 Ethyl phenylmalonate, 16, 33 18, 84 Ethyl phenyloxaloacetate, 16, 33 Ethyl phthalimidomalonate, 14, 58 Ethyl pjmelate, 11, 42 17, 91 Ethyl propanetetracarboxylate, 10, 58 Ethyl propionate, 17, 34 Ethyl tso-propylmalonate, 11, 20, 21 Ethyl salicylate, 10, 51 11, 43 Ethyl sebacate, 14, 20 Ethyl sodium phthalimidomalonate, 14, 58... 

Serine has been prepared by the Strecker method from glycol-aldehyde 1 and from ethoxyacetaldehyde,2 3 by the condensation of ethyl formate with ethyl hippurate followed by reduction and hydrolysis,4 5 from the reaction product of chloromethyl ether with ethyl sodium phthalimidomalonate,6 and by amination of a-bromo-/3-methoxypropionic acid with subsequent demethyla-tion.7... 

Trinitroanisole Complex, CHj O-CgHjtNOjJj -[ 3CHAcNaCOaC1Hs, red amor ppt, expl on j heating sol in ale or acet. It was obtained on I treating a benzolic soln of TNAns with a ben2olic soln of ethyl sodium acetate. Another expl complex was obtained on treating TNAns with ethyl sodium malonate Ref C.L. Jackson Si F.H.Gazzolo, Amer Chem-J 23, 376(1900) JCS 78, I, 433-4(1900)... 

Ml - MERCURY. 11o-CARBOXYPHENYL >THIO)ETHYL- SODIUM SALT RN - 54-64-8... 

Ionic organic compounds involving carbanions react readily with oxygen. For example, ethyl-sodium, C2Hj Na+, self-ignites in air. Ionic organometallic compounds are extremely reactive in water, as shown by the following reaction ... 

Chemical Name Barbituric acid, 5-sec-butyl-5-ethyl-, sodium salt... 

Substitution of alkyl groups. In some cases, an organic group will replace a different alkyl group from an organometallic compound. For example, the reaction of ethyl sodium and benzene can be shown as follows ... 

The German process of manufacturing this compound was complicated and eompri.sed the following principal steps (1) the conversion of ethyl chloride into ethyl sodium arsenate by treatment with sodium arsenate under pre.ssurc (2) reduction to ethyl arsenious oxide by the action of sulfurous acid (3) conversion of the ethyl araenious oxide to ethyl dichlorarsine by treatment with hydrochloric acid. 

Silicon triethyl ethyl ether or Silicoheptyl ethyl ether, (CgHs) Si(OC2H5), is obtained by the interaction of zinc ethyl, sodium, and silicon diethyl diethyl ether, ( 2115)281(0.02115)2. It is a colourless liquid, B.pt. 153° C., density 0 8414, 0-8393, 0 8403 at 0° C., insoluble in water, miscible with alcohol or ether, and stable in air. Acetyl chloride acting on the compound gives rise to tri ethyl silicon chloride. 

In case of the direct reaction of the natural oil or lower alkyl ester of natural fatty acid and the amine the reaction method for producing the amide derivatives is as follows That is, about 1 mol of the said oils and 1 to 100 equivalent mols of the said amines are mixed in the absence or presence of solvents such alcohols as methanol, ethanol or the like, such aromatic hydrocarbons as benzene, toluene, xylene or the like, such halogenoalkanes as methylene chloride, chloroform, carbon tetrachloride or the like, and such alkenes or alkanes as petroleum ether, benzene, gasoline, ligroin or cyclohexane, such ethers as tetrahyrofuran, dioxane and the like, or a mixture thereof, and the mixture is subjected to the reaction in the absence or presence of catalyst amount or equimolar amount to the amine of an auxiliary agent of condensation, such as alkoholate of alkali metal, i.e. lithium, methylate, lithium ethylate, sodium methylate, sodium ethylate, potassium-t-butylate and the like, or acidic auxiliary agents, i.e. p-toluenesulfonic acid and the like, thereby to yield the amide derivatives. In this reaction, a formal alcohol may be removed from the reaction system. 

Only a few reports are available on reactions via acylsodium derivatives. Wanklyn [47] carried out a reaction of ethyl sodium, formed from Et2Zn and metallic sodium, with CO and observed the formation of diethyl ketone (Eq. (5.43)). Later, Schluback prepared ethyl sodium from ethyl mercury and metallic sodium and then reacted it with CO. Triethylcarbinol was obtained in addition to diethyl ketone [48], Ryang and Tsutsumi [49] reported the formation of different compounds for reactions using different solvents (Eqs. (5.44) and (5.45)). 

In conclusion it should be pointed out that the unusual success of the Wurtz-Fittig reaction in coupling two unlike halides can be understood if we assume that phenyl sodium predominates over the alkyl sodium in the first phase of the reaction and that phenyl sodium reacts preferentially with alkyl halides in the second phase of the reaction. These assumptions seem very reasonable, since arbmatic halides are always more inert to displacement reactions than alkyl halides and ethyl sodium has been shown to react even with benzene to give phenyl sodium and ethane.11 Consequently, when a solution of ethyl bromide and bromo-... 

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