Ethyl reactions with

This ion (1) can react in three ways, according to the conditions. (a) reaction with the HSOj may give ethyl hydrogen sulphate... 

The reaction with ethyl iodide is less rapid and it is necessary to warm the mixture gently until cloudy. On cooling, crystals of the ethiodide are formed, and after recrystallisation from methylated spirit have m.p. 84 . 

The formation of ethyl acetoacetate is an example of a general reaction knowu as the acetoacetlc ester condensation in which an ester having hydrogen on the a-carbon atom condenses with a second molecule of the same ester or with another ester (which may or may not have hydrogen on the a-carbon atom) in the presence of a basic catalyst (sodium, sodium ethoxide, sodamide, sodium triphenylmethide) to form a p-keto-ester. The mechanism of the reaction may be illustrated by the condensation of ethyl acetate with another molecule of ethyl acetate by means of sodium ethoxide. ... 

The formation of ethyl isopropylidene cyanoacetate is an example of the Knoevenagel reaction (see Discussion before Section IV,123). With higher ketones a mixture of ammonium acetate and acetic acid is an effective catalyst the water formed is removed by azeotropic distillation with benzene. The essential step in the reaction with aqueous potassium cyanide is the addition of the cyanide ion to the p-end of the ap-double bond ... 

Apparatus 250-ml round-bottomed flask for the cleavage of THF 500 ml flask (see Fig. 1) for the coupling with ethyl vinyl ether 1-1 flask (see Fig. 1) for the reaction with allenyl1ithiurn 500-ml round-bottomed flask for the deprotection. 

One route to o-nitrobenzyl ketones is by acylation of carbon nucleophiles by o-nitrophenylacetyl chloride. This reaction has been applied to such nucleophiles as diethyl malonatc[l], methyl acetoacetate[2], Meldrum s acid[3] and enamines[4]. The procedure given below for ethyl indole-2-acetate is a good example of this methodology. Acylation of u-nitrobenzyl anions, as illustrated by the reaction with diethyl oxalate in the classic Reissert procedure for preparing indolc-2-carboxylate esters[5], is another route to o-nitrobenzyl ketones. The o-nitrophenyl enamines generated in the first step of the Leimgruber-Batcho synthesis (see Section 2.1) are also potential substrates for C-acylation[6,7], Deformylation and reduction leads to 2-sub-stituted indoles. 

There are also palladium-catalysed procedures for allylation. Ethyl 3-bromo-l-(4-methylphenylsulfonyl)indole-2-carboxylate is allylated at C3 upon reaction with allyl acetate and hexabutylditin[27], Ihe reaction presumably Involves a ir-allyl-Pd intermediate formed from the allyl acetate, oxidative addition, transmetallation and cross coupling. 

Potts et al. (333) condensed dipolarophiles (DMA, dibenzoylacetylene, ethyl propiolate) with ylides (81) obtained by quaternization of 4-methyl-thiazole with an a-bromoketone or ester and subsequent deprotonation. In fact the 1 1 molar adduct obtained (82) rearranged to a pyr-rolothiazine (83). One example of this reaction is described Scheme 49. 

Reaction of ethyl iodide with triethylamine [(CH3CH2)3N ] yields a crystalline compound CgH2oNI in high yield This compound is soluble in polar solvents such as water but insoluble in nonpolar ones such as diethyl ether It does not melt below about 200°C Suggest a reasonable structure for this product... 

Reaction with ammonia and amines (Sec tion 20 12) Esters react with ammonia and amines to form amides Methyl and ethyl esters are the most reactive... 

Esters of nonenolizable monocarboxylic acids such as ethyl benzoate give p diketones on reaction with ketone enolates... 

Give the structure of the product formed on reaction of ethyl acetoacetate with each of the following... 

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