Ethyl phenylacetate reduction

Silver fluoborate, reaction with ethyl bromide in ether, 46, 114 Silver nitrate, complexing with phenyl-acetylene, 46, 40 Silver oxide, 46, 83 Silver thiocyanate, 45, 71 Sodium amide, in alkylation of ethyl phenylacetate w ith (2-bromo-ethyl)benzene, 47, 72 in condensation of 2,4-pentanedione and 1 bromobutane to give 2,4-nonanedione, 47, 92 Sodium 2 ammobenzenesulfinate, from reduction of 2 mtrobenzenesul-finic acid, 47, 5... 

The general procedure used for the synthesis of [l,2,3]triazolo[l,2-tf][l,2,4]benzotriazin-l-5(6//)-dione derivatives 506 is shown in Scheme 86. Ionic 1,3-dipolar cycloaddition of the appropriate azide 503 to ethyl phenylacetates gives l-(2-nitrophenyl)-4-aryl-5-oxo[l,2,3]triazoles 504. Catalytic reduction of these compounds affords the corresponding amines 505. Cyclocondenzation of these amines to the final tricyclic compounds 506 is performed using triphosgene in anhydrous tetrahydrofuran solution at room temperature (Scheme 86) <2005JME2936>. 

The pyridine derivatives (183) underwent addition reactions with ethyl phenylacetate to give adducts 184, which could be reductively cyclized in the presence of a platinum catalyst, to give the indolizidines 185.2 3... 

Reduction. The reagent is useful for reduction of carboxylic acid esters to primary alcohols. For example, the following esters have been reduced to the corresponding carbinols ethyl p-nitrobenzoate (96% yield), ethyl phenylacetate (90% yield), ethyl gly-cinate (70% yield). The reaction has some useful features Hydroxylic solvents (ethanol, water) can be used, the selectivity is higher than in the case of lithium aluminum hydride, and the reagent is nearly neutral. The reagent was found to be satisfactory for reduction of the dimethyl ester of 4,4 -dinitro-2,2 -diphenic acid (la) to the corresponding alcohol (lb, 51%yield).2... 

Pbenethyl Alcohol. Benzeneethanol 2-phenyleth-anol 0-phenylethyl alcohol benzyl carbtnol d-hydroxyeth -y I benzene. C,H O mol wt 122.16. C 78.65%, H 8.25%, O 13.10%. Found in a number of natural essential oils, such as rose, carnation, hyacinth, Aleppo pine, orange blossom, geranium Bourbon, neroli and in the essentia] oil of cham-paca. Prepd by reduction of ethyl phenylacetate with sodium in abs alcohol Bouveault, Blanc, Bull Soc. Chim. [3]... 

Reductions of keto esters to esters are not very frequent. Both Clemmensen and Wolff-Kizhner reductions can hardly be used. The best way is desulfurization of thioketals with Raney nickel (p. 130). Thus ethyl acetoacetate was reduced to ethyl butyrate in 70% yield, methyl benzoylformate (phenylglyoxy-late) to methyl phenylacetate in 79% yield, and other keto esters gave equally high yields (74-77%) [82J]. 

Enholm [13] has also described the synthesis of soluble designer supports by the ring-opening metathesis polymerization (ROMP) of norbornyl derivatives. Reduction of norbornene-l-carboxaldehyde 88 to the corresponding alcohol 89, followed by treatment with either 2-bromopropionic acid or 2-bromo-2-phenylacetic acid in the presence of DCC, provided the esters 90 or 91 respectively (Scheme 19). Polymerization of 90 and 91 was carried out with Grubbs catalyst and halted after 25 s by capping with excess ethyl vinyl ether to give polymers 92 and 93 respectively. 

Acyl radicals and acyl anions are proposed intermediates in the reduction of phenylacetyl chloride and hydrocinnamoyl chloride at mercury in MeCN [223]. Among the products obtained from the reduction of phenylacetyl chloride are 1,4-diphenyl-2-butene-2,3-diol diphenylacetate, phenylacetaldehyde, toluene, 1,3-diphenyl-acetone, and l,4-diphenyl-2,3-butanediol, as well as phenylacetic acid and phenylacetic acid anhydride. Analogous products arise from the reduction of hydrocinnamoyl chloride l,6-diphenyl-3-hexene-3,4-diol dihydrocinnamate, hydrocinnamaldehyde, ethyl benzene, l,6-diphenyl-3,4-hexanediol, hydrocinnamic acid, and hydrocinnamic acid anhydride. 

Derivation (1) By reduction of phenylacetic ethyl ester by sodium in absolute alcohol. (2) By the action of ethylene oxide on phenylmagnesium bromide and subsequent hydrolysis. (3) Component of many essential oils. 

The parent base, morphan, has been synthesized as follows. Condensation of m-nitrobenzaldehyde with benzoyl chloride and sodium cyanide yielded [cxl], which was converted to [cxli] and hydrogenated over Raney nickel at 200° C. to give [cxt.tt] the latter was then reduced to morphan [cxliji] with hydrogen and copper chromite [45], Morphan may be more simply prepared by the hydrogenation of ethyl m-nitro-phenylacetate over platinum oxide, followed by reduction of the [oxui] so formed by lithium aluminium hydride [40],... 

Ethyl diazophenylacetate is reduced to phenylacetate in aqueous dioxane at pH 7 (Jugelt et al., 1972). The authors reported that dinitrogen is formed, clearly indicating that the mechanism of this reduction is different from that of 2-diazo-l-phenylethan-l-one. Under aprotic conditions (sulfolane), ethyl diazoacetate, but... 

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