ETHYL GLYCIDATE

The purity of the ethyl glycidate prepared according to this procedure was... 

Using benzyl bromide as the alkylation agent, the corresponding benzyl glycidate is obtained in 60% yield.1 2 3 4 5 16 In contrast with ethyl glycidate, this compound is not stable to distillation however, it can be purified by chromatography on silica gel. 

Ethyl glycidate Oxiranecarboxylic acid, ethyl ester, (R)- (12) (111058-33-4) (S)-Serine L-Serine (8,9) (56-45-1)... 

Ethyl glycidate is a rather sensitive compound (it cannot be chromatographed on silica gel) and distillation at low temperature under high vacuum (0.1-2 mm) avoids the formation of undistillable residues resulting from polymerization. The product should be stored at 5°C (or lower) and is perfectly stable at this temperature. 

This procedure describes an efficient method for the synthesis of >99% enantiomerically pure ethyl glycidate from L-serine. Although preparation of potassium glycidate via cyclization of 3-bromo-2-hydroxypropionic acid,2 and from 3-chloro-2-hydroxypropionic acid (obtained by microbial reduction of chloropyruvic acid)3 was previously reported, the corresponding ethyl ester was never described. An enantioselective synthesis of the 2,3-epoxy acid by oxidation of 2,3-epoxypropanol has also been reported.4... 

ETHYL GLYCIDATE FROM (S)-SERINE ETHYL (R)-(+)-2,3-EPOXYPROPANOATE... 

The purity of the ethyl glycidate prepared according to this procedure was >97% as measured by gas chromatography (BP5 capillary column from SGE). The enantiomeric purity was greater than 99% ee as determined by chiral gas chromatography on a 50-m CYDEX-B capillary column (0-cyclodextrin stationary... 

Aluminum chloride Ethyl glycidate N-Chlorodiisopropylamine Hexamethylphosphoramine Sodium borohydride Dimethylacetamide... 

A mixture of 24.2 g of the product of Step 1, 1.2 liters of ethanol and 19.2 g of ethyl glycidate was refluxed under an inert atmosphere for 4 hours and was then evaporated to dryness under reduced pressure. The oil was chromatographed over silica gel and was eluted with a 7-3 benzene-ethyl acetate mixture to obtain 28.2 g of ethyl 4RS-trans-2-hydroxy-3-[(5-hydroxybenzyl)-l,2,2a,3,4,5-hexahydro-benz[c,d]indol-4-yl )-methylamino]-propanoate. 

Ethyl Glycidate from (S)-Serine (Ft)-(+)-Ethyl 2,3-Epoxypropanoate. Y. Petit and M. Larchev6que, Laboratoire de Synthase Organique, (URA 1381 du CNRS), E.N.S.C.P., 11, rue Pierre et Marie Curie,... 

Vogl (112. 113) is developing an ingenious preparative method for ionomers synthesis by copolymerization of ethyl glycidate with other cyclic ethers and then hydrolysis of the pendant ester groups. 

With the same aim of preparing polyTXN ionomers Vogl and MacKnight studied the copolymerization of TXN with ethyl glycidate 144,145). The copolymers were subsequently converted to the corresponding polyacids ... 

Trimethylene Glycol. 1,3-Propanediol. CjHt02 mol wt 76.09. C 47.35%, H 10.60%, O 42.05%. HOCH2-CH2CHjOH. Prepd by reduction of ethyl glycidate with lithium aluminum hydride Walborsky, Colombini, J. Org... 

Azide is a potent nucleophile and can react with electrophilic substrates other than halides and sulfonate esters. Reaction of azide with the epoxide moiety in carboethoxy oxirane (ethyl glycidate) was followed by catalytic hydrogenation of the azide and hydrolysis of the ester to give isoserine (3-amino-2-hydroxypropanoic acid, 1.23). This synthetic approach to isoserine dates to 1879. 3... 

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