Method of preparing catalyst for obtaining 3-acetylheptane-2,6-dione and method of obtaining 3-acetylheptane-2,6-dione with application of obtained catalyst

FIELD: chemistry.

SUBSTANCE: claimed invention relates to field of chemistry of ketones, in particular, to method of preparing catalyst for obtaining 3-acetylheptane-2,6-dione and to method of obtaining 3-acetylheptane-2,6-dione with application of obtained catalyst. Described are: method of preparing microdimensional catalyst for obtaining 3-acetylheptane-2,6-dione, which consists in dissolution of cerium chloride hydrate of formula CeCl3×7H2O in methyl alcohol with further removal of solvent by its evaporation for 1 hour at temperature 90°C and heating residue for 1.5 hour at temperature 150°C, and method of obtaining 3-acetylheptane-2,6-dione by interaction of acetylacetone with methylvinylketone in presence of obtained catalyst, process being carried out with molar ratio acetylacetone: methylvinylketone: catalyst in terms of CeCl3×7H2O equal 1:1:0.1-0.2.

EFFECT: increased output of 3-acetylheptane-2,6-dione to 76-87% due to application of obtained catalyst, nearly 3-fold reduction of amount of used catalyst, carrying out process of obtaining 3-acetylheptane-2,6-dione without solvent, as well as reduction of time of process carrying out, which makes process cheaper and reduces ecological load onto environment.

2 cl, 4 ex

 

The present invention relates to the field of chemistry ketones, particularly, to a method of preparation of a catalyst to obtain 3-acetylated-2,6-dione (I) and to a method for producing 3-acetylated-2,6-dione, the founder of class β,δ-triketones, which find application in the synthesis of peroxides with antiparasitic activity [Katrin Ingram, Ivan Andreevich Yaremenko, Igor Krylov, Lorenz Hofer, Alexander Olegovich Terent'ev, Jennifer Keiser. Identification of antischistosomal leads by evaluating peroxides of β-dicarbonyl compounds and their heteroanalogs: bridged 1,2,4,5-tetraoxanes and alphaperoxides, and β,δ-triketones: tricyclic monoperoxides. J. Med. Chem. 2012, DOI: 10.1021/jm3009184], heterocyclic compounds used in food and medicinal chemistry [Niigata Kunihiro, Tatsuya Maruyama, Shikama Hisataka, Takasu Toshiyuki, Umeda Masako, Hirasaki Eiko, Hayashibe Satoshi, Kimura Takenori, Pyrazole derivatives and compositions and methods of use as the maillard reaction inhibitors, US 5453514(A); Frederic Lieby-Muller, Christophe Allais, Thierry Constantieux, Jean Rodriguez, Metal-free Michael addition initiated multicomponent oxidative cyclodehydration route to polysubstituted pyridines from 1,3-dicarbonyls. Chem. Commun. 2008, 4207-4209], in the synthesis oxabicyclo systems - analogues of natural products with anti-parasitic activity [Albert Padwa, Zhijia J. Zhang, Lin Zhi, Cyclization-Cycloaddition Cascade of Rhodium Carbenoids Using Different Carbonyl Groups. Highlighting the Position of Interaction, J. Org. Chem. 2000, 65, 5223-5232] and in the synthesis present in the bicyclic alkaloids fragments [Remain Noel, Corinne Vanucci-Bacque, Marie-Claude Fargeau-Bellassoued, Gerard Lhommet, Synthesis of New Chiral 6-Carbonyl 2,3,8,8a- - Tetrahydro-7H-oxazolo[3,2-a]pyridines, J. Org. Chem., 2005, 70, 9044-9047].

A method of obtaining 3-acetylated-2,Diana by the interaction of methyl vinyl ketone are with acetylacetone in the presence of a catalyst reaction - ionic liquid [Brindaban C. Ranu, Subhash Banerjee. Ionic Liquid as Catalyst and Reaction Medium. The Dramatic Influence of a Task-Specific Ionic Liquid, [BmIm]OH, in Michael Addition of Active Methylene Compounds to Conjugated Ketones, Carboxylic Esters, and Nitriles. Organic Letters, 2005, 7, 3049-3052] according to this method, the methyl vinyl ketone are (6 mmol) are added to a mixture of acetylacetone (5 mmol) and ionic liquid 1-butyl-3-methylimidazolium hydroxide [BmIm]OH (3 mmol) in 0.5 hours to produce a product with a yield of 95%. The disadvantage of this method is the use of very expensive catalyst reaction - ionic liquid, which previously specially obtained from 1-butyl-3-methylimidazolium bromide [BmIm]Br.

Also known is a method of obtaining 3-acetylated-2,6-dione [Anima Boruah, Mukulesh Baruah, Dipak Prajapati, Jagir S. Sandhu. Cerium Catalyzed Michael Addition of 1,3-Dicarbonyl Compounds Under Microwave Irradiation. Synthetic Communications 1998, 28, 653-658] according to which a mixture of acetylacetone (10 mmol), methyl vinyl ketone are (10 mmol) and catalyst of cerium chloride (III) (1 mmol) was subjected to microwave irradiation frequency of 2450 MHz for 8 minutes, resulting in the received target product with a yield of 92%. The disadvantage of this method is the use of expensive equipment to generate microwave radiation, unspecified reaction temperature and radiation power, which can lead to non-repeatable result.

Known catalytic system CeCl3×7H2O (0.2 equivalent) / NaI (0.1 equivalent) to obtain 3-acetyl shall heptan-2,6-dione and the method of obtaining 3-acetylated-2,6-dione [Giuseppe by Bartoli, Marcella Bosco, Maria Cristina Bellucci, Enrico Marcantoni, Letizia Sambri, Elisabetta Torregiani. Cerium (III) Chloride Catalyzed Michael Reaction of 1,3-Dicarbonyl Compounds and Enones in the Presence of Sodium Iodide Under Solvent-Free Conditions. Eur. J. Org. Chem. 1999, 617-620] whereby a target product was obtained by interaction of acetylacetone with methyl vinyl ketone are using a catalytic system CeCl3×7H2O (0.2 equivalent) / NaI (0.1 equivalent), obtained by mixing the two reagents. The reaction time for obtaining the target product 6 hours, the product yield was 97%. The disadvantage of this method is the use of additional reagent upon receipt of the catalyst NaI, which increases the cost and complicates the process of obtaining the target product. In addition, it is not clear what is the catalyst for this reaction; they can act and CeI3. In [Fukuzawa, S.-i, Fujinami T., Sakai S. Carbon-carbon bond formation between a-halogenoketones and aldehydes promoted by cerium (III) iodide or cerium (III) chloride-sodium iodide. J. Chem. Soc., Chem. Commun. 1985, 777-778] shows a similar mechanism of action CeI3and systems CeCl3/NaI related to the invention, the processes involving enol form of the carbonyl compounds.

In this paper we propose a catalyst CeCl3×7H2O to obtain 3-acetylated-2,6-dione [Giuseppe by Bartoli, Marcella Bosco, Maria Cristina Bellucci, Enrico Marcantoni, Letizia Sambri, Elisabetta Torregiani. Cerium (III) Chloride Catalyzed Michael Reaction of 1,3-Dicarbonyl Compounds and Enones in the Presence of Sodium Iodide Under Solvent-Free Conditions. Eur. J. Org. Chem. 1999, 617-620], and the e described and adopted us for the prototype method for producing 3-acetylated-2,6-dione according to which the target product was obtained by interaction of acetylacetone (1.1 mmol) with methyl vinyl ketone are (1 mmol) in acetonitrile using catalyst CeCl3×7H2O, taken in stoichiometric quantity. The reaction time of 96 hours, the yield of the desired product 30%. The disadvantage of the catalyst is its low efficiency and, as a consequence of the low yield of the target product, and the duration of the process of obtaining 3-acetylated-2,6-dione.

The present invention is to develop a method of preparation of effective micro-size particles of the catalyst for use in the method of obtaining 3-acetylated-2,6-dione with high output.

This object is achieved by the proposed method of preparation of micro-size particles of a catalyst to obtain 3-acetylated-2,6-dione, which consists in the fact that the hydrate cerium chloride formula CeCl3×7H2O is dissolved in methyl alcohol and subsequent removal of solvent by evaporation in the course of 1 hour at a temperature of 90°C and heat balance for 1.5 hours at a temperature of 150°C.

Also we propose a method for the preparation of 3-acetylated-2,6-dione by the interaction of acetylacetone with methyl vinyl ketone are in the presence of cerium catalyst, characterized in that as cerium catalyst using the catalyst and the process is carried out at a molar ratio of acetylacetone: methyl vinyl ketone are: catalyst in terms of CeCl3×7H2O = 1:1:0.1 to 0.2. The% is with proceeds according to the following scheme:

The process was performed at room temperature (20-25°C) for 6-12 hours.

The estimated chemical composition of the obtained micro-size particles of the catalyst can be represented by the following formula nCeCl3/mCeOCl/×H2O, where n=0.6 to 0.9; m=0.1 to 0.4; x=3-5, as from literature data it is known that the CeCl3×7H2O when heated above 90°C, first, loses water, and secondly, interacts with its hydrated by water with formation CeOCl [Gmelin-Friedheim-Peters. Bd. VI.2. Abt.7. Aufl. str].

The technical result is an increase in the yield of 3-acetylated-2,6-dione to 76-87% due to the use of the obtained catalyst nCeCl3/mCeOCl/×H2O reducing the number CeCl3×7H2O approximately three times and the process for the preparation of 3-acetylated-2,6-dione without solvent and decrease the duration of the process, which reduces the process and reduces the environmental burden on the environment.

The invention meets the criterion of "novelty", as known in the scientific-technical and patent literature does not include a full set of features characterizing the present invention. The present invention meets the criterion of "inventive step", because up to the present time microcrystalline system prepared from commercially DOS is available CeCl 3×7H2O, was not known as a catalyst. Moreover, it was impossible to predict in advance that obtained by the proposed method, the catalyst is more effective to catalyze the 3-acetylated-2,6-dione, than the original for this system CeCl3×7H2O and that the reaction to proceed in the absence of a solvent with a high yield of the target product.

The invention meets the condition of "industrial applicability", as the 3-acetylated-2,6-dione is the founder of (3,5-triketones and finds application in the synthesis of peroxides with antiparasitic activity and heterocyclic compounds used in medicinal chemistry.

The invention is illustrated by the following examples without limiting its scope.

Example 1. Obtaining micro-size particles of catalyst

1 gram CeCl3×7H2O was dissolved in 5 ml of Meon. The solution was heated in the flask to evaporate the solvent for 1 hour at a temperature of 90°C, then another 1.5 hours at a temperature of 150°C. as a result received 720 mg micro-size particles of the catalyst, the chemical composition of which can be represented by the following formula nCeCl3/mCeOCl/×H2O, where n=0.6 to 0.9; m=0.1 to 0.4; x=3-5.

Example 2 (comparative). Obtaining 3-acetylated-2,6-dione I CeCl3×7H2O

To 500 mg (5 mmol) of acetylacetone with stirring EXT is ulali 350 mg (5 mmol) of methyl vinyl ketone are, then, under vigorous stirring was added 186,3 mg (0.5 mmol) CeCl3×7H2O. the Molar ratio of the reagents acetylacetone: methyl vinyl ketone are: CeCl3×7H2O=1:1:0,1. The reaction mixture was stirred for 12 hours. To the reaction mass was added 20 ml of a mixture of petroleum ether - ethyl acetate (volume ratio 1:2, respectively). The precipitate was filtered and washed with 30 ml of a mixture of petroleum ether - ethyl acetate (volume ratio 1:2, respectively). The filtrates were combined, evaporated in a water jet vacuum pump. From the resulting reaction mass was shooting range1H NMR where 3-acetylated-2,6-dione was observed in trace quantities.

Example 3. Obtaining 3-acetylated-2,6-dione (I, using the obtained catalyst

To 500 mg (5 mmol) of acetylacetone with stirring was added 350 mg (5 mmol) of methyl vinyl ketone are, then, under vigorous stirring was added micro-size particles of the catalyst obtained from 186,3 mg (0.5 mmol) CeCl3×7H2O. the Ratio of reagents acetylacetone: methyl vinyl ketone are: the catalyst in terms of CeCl3×7H2O=1:1:0,1. The reaction mixture was stirred for 6 hours. To the reaction mass was added 10 ml of a mixture of petroleum ether - ethyl acetate (volume ratio 1:2, respectively). The precipitate was filtered, then washed with 30 ml of a mixture of Petro is any ether - ethyl acetate (volume ratio 1:2, respectively). The combined filtrates evaporated in a water jet vacuum pump. 3-Acetylated-2,6-dione was isolated by column chromatography on SiO2using eluent petroleum ether - ethyl acetate of increasing the share of the latter from 40 to 80% on. Received 3-acetylated-2,6-dione (649 mg, 3,23 mmol), yield 76%.

1H NMR (300.13 MHz, CDCl3), δ: 1.97-2.16 (m, 11N), 2.40 (t, 2H, J=7.0 Hz), 3.63 (t, N, J=7.0 Hz), 16.64 (USS, N).

Example 4. Obtaining 3-acetylated-2,6-dione I

To 500 mg (5 mmol) of acetylacetone with stirring was added 350 mg (5 mmol) of methyl vinyl ketone are, then, under vigorous stirring was added micro-size particles of the catalyst obtained from 372,6 mg (1 mmol) CeCl3×7H2O. the Ratio of reagents acetylacetone: methyl vinyl ketone are: the catalyst in terms of CeCl3×7H2O=1:1:0,2. The reaction mixture was stirred for 12 hours. To the reaction mass was added 10 ml of a mixture of petroleum ether - ethyl acetate (volume ratio 1:2, respectively). The precipitate was filtered, then washed with 30 ml of a mixture of petroleum ether - ethyl acetate (volume ratio 1:2, respectively). The combined filtrates evaporated in a water jet vacuum pump. 3-Acetylated-2,6-dione was isolated by column chromatography on SiO2using eluent petroleum ether - ethyl shall zitat increasing the share of the latter from 40 to 80% on. Received 740 mg (3,70 mmol) 3-acetylated-2,6-dione, yield 87%. (proof of product produced).

1. Method of preparation of micro-size particles of a catalyst to obtain 3-acetylated-2,6-dione, which consists in the fact that the hydrate cerium chloride formula CeCl3·7H2O is dissolved in methyl alcohol, followed by removal of solvent by evaporation for 1 h at 90°C and heat balance for 1.5 h at 150°C.

2. The method of obtaining 3-acetylated-2,6-dione by the interaction of acetylacetone with methyl vinyl ketone are in the presence of cerium catalyst, characterized in that as cerium catalyst using the catalyst obtained according to claim 1, and the process is carried out at a molar ratio of acetylacetone:methyl vinyl ketone are:catalyst obtained according to claim 1, in terms of CeCl3·7H2O = 1:1:0.1 to 0.2.



 

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