Acetoacetates methyl ester

SYNS ACETOACETIC METHYL ESTER METHYL-ACETOACETATE METHYL ACETYLACETONATE METHYH3-OXOBUTYRATE 3-OXOBUTANOIC ACID METHYL ESTER... 

Acetoxetic xid, methyl ester Acetoacetic methyl ester AI3-06000 Butanoic xid, 3-oxo-, methyl ester CCRIS 2302 EINECS 203-299-8 HSDB 1083 Methyl 3-oxobutxoate Methyl 3-oxobutyrate Methyl xeto-acetate Methyl acetylxetate Methyl acetylacetonate Methylxetoacetate Methylester kyseliny xetxtove. Solid mp = 27.5° bp = 171.7° 6 = 1.0762 Xm = 240 nm (e = 1514, EtOH) xluble in CCI4, very soluble in H2O, freely soluble in EtOH, Et20. 

Ethyl Acetoacetate. -The e. planation of the manner in which this substance is produced has been given in the account of the preparation. The result was anived at, not by the iscila-tion of the intermediate compound formed by the union of ethyl acetate with sodium ethylate, but by analogy with the behaviour of benzoic methyl ester with sodium benzylate, which gave the same additive product as that obtained by combining benzoic benzyl ester with sodium methylate, showing that such combinations could occur,... 

Acetoacetic acid N-benzyl-N-methyiaminoethyl ester -Aminocrotonic acid methyl ester m-Nitrobenzaldehyde... 

A mixture of 4.98 g of acetoacetic acid N-benzyl-N-methylaminoethyl ester, 2.3 g of aminocrotonic acid methyl ester, and 3 g of m-nitrobenzaldehyde was stirred for 6 hours at 100°C in an oil bath. The reaction mixture was subjected to a silica gel column chromatography (diameter 4 cm and height 25 cm) and then eluted with a 20 1 mixture of chloroform and acetone. The effluent containing the subject product was concentrated and checked by thin layer chromatography. The powdery product thus obtained was dissolved in acetone and after adjusting the solution with an ethanol solution saturated with hydrogen chloride to pH 1 -2, the solution was concentrated to provide 2 g of 2,6-dimethyl-4-(3 -nitrophenyl)-1,4-dihydropyridlne-3,5-dicarboxylic acid 3-methylester-5- -(N-benzyl-N-methylamino)ethyl ester hydrochloride. The product thus obtained was then crystallized from an acetone mixture, melting point 136°Cto 140°C (decomposed). 

Nitrobanzaldehyde Acetoacetic acid methyl ester Ammonia... 

Acetoacetic acid methyl ester Nifedipine Acetoacetic ester Dipyridamole Acetoin... 

The diazo transfer reaction between p-toluenesulfonyl azide and active methylene compounds is a useful synthetic method for the preparation of a-diazo carbonyl compounds. However, the reaction of di-tert-butyl malonate and p-toluenesulfonyl azide to form di-tert-butyl diazomalonate proceeded to the extent of only 47% after 4 weeks with the usual procedure." The present procedure, which utilizes a two-phase medium and methyltri-n-octylammonium chloride (Aliquat 336) as phase-transfer catalyst, effects this same diazo transfer in 2 hours and has the additional advantage of avoiding the use of anhydrous solvents. This procedure has been employed for the preparation of diazoacetoacetates, diazoacetates, and diazomalonates (Table I). Ethyl and ten-butyl acetoacetate are converted to the corresponding a-diazoacetoacetates with saturated sodium carbonate as the aqueous phase. When aqueous sodium hydroxide is used with the acetoace-tates, the initially formed a-diazoacetoacetates undergo deacylation to the diazoacetates. Methyl esters are not suitable substrates, since they are too easily saponified under these conditions. 

Methyl acetoacetate Acetoacetic acid, methyl ester (8) Butanoic acid, 3-oxo-, methyl ester (9) (105-45-3)... 

Nicardipine Nicardipine, l,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-methyl-2-[(methyl-phenylmethyl)-amino]ethyl ester 3,5-pirididincarboxylic acid (19.3.7), is synthesized in a manner analogous to the synthesis of nifedipine, the only difference being that in the Hantsch synthesis, two different )3-dicarbonyl compounds are used simultaneously with o-nitrobenzaldehyde. During this, one of these in the enamine form of acetoacetic ester is simultaneously used as an amine component. A heterocycUzation reaction is accomplished by reacting, the methyl ester of 8-aminocrotonic acid with the 2-methyl-2-benzyl-aminoethyl ester of acetoacetic acid [24-27]. 

Isodehydroacetic acid has been prepared by the action of sulfuric acid on acetoacetic ester 3 4 The ethyl ester has been prepared by the action of dry hydrogen chloride on acetoacetic ester 6 6 and by the sodium-catalyzed condensation of ethyl /3-chloroisocrotonate with ethyl acetoacetate3 The methyl ester of isodehydroacetic acid has been prepared by the thermal rearrangement of pyrazolines 7... 

A soln. of 4-amino-4 -chlorodiphenylmethane, methyl acetoacetate, and one drop of 5%-HOI in methylene chloride refluxed until no more water is collected in a water separator —y methyl / -(4-p-chlorobenzyl-anilino)-crotonate. Y 97%.—The methyl esters give better yields than the ethyl esters, both in the above condensation, and in a following ring closure to quinolines (cf. 5, 614). (F. e. s. C. E. Kaslow and R. D. Stayner, Am. Soc. 70, 3350 (1948).) s. a. 4, 750... 

ACETOACETIC ACID, METHYL ESTER (105-45-3) Combustible liquid (flash point 170°F/77°C). Moisture may cause decomposition. Incompatible with oxidizers, strong acids, nitrates. 

Variations of the malonic ester and acetoacetic ester sequenees lead to many useful synthetic opportunities. In the examples quoted, the base-solvent pair used was ethanol-sodium ethoxide, where the alkoxide is the conjugate base of tbe solvent. If NaOEt-EtOH were used with a methyl ester, transesterification would give a mixture of methyl and ethyl esters as products. For both malonic ester and acetoacetic ester removal of the most acidic proton (a to both carbonyls) also gives the more thermodynamically stable enolate. Either NaOEt-EtOH or LDA-THF will generate the desired enolate. The malonic ester synthesis is most useful for the synthesis of highly substituted monoacids, and tbe acetoacetic ester synthesis is used to prepare substituted methyl ketones. 

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