The method of obtaining substituted 1-ethylaminoethanol

 

(57) Abstract:

Describes how to obtain the substituted 1-ethylaminoethanol General formula (1), where R=n-C6H13the h8H17Ph, wherein the substituted allene General formula R-==, where R is as defined above, is subjected to the interaction with triethylaluminium Et3Al in a molar ratio R-==:Et3Al=10: (10-14), respectively, in the presence of a catalyst of zirconatetitanate (Cf2ZrCl2) in an amount of 2-6 mol. % with respect to substituted Allen and the reaction is performed in the environment of methylene chloride in an argon atmosphere at room temperature ~ 20oC and normal pressure for 8-12 hours the New compounds may find application as components of catalytic systems in the processes of oligo - and polymerization of olefin, diene and acetylene hydrocarbons, and fine organic and ORGANOMETALLIC synthesis. 1 PL.

The present invention relates to methods for new alyuminiiorganicheskikh compounds (AOC), specifically to a method for producing 1-ethylaminoethanol General formula (1)

,

where R=n-C6H13H-C8H17Ph

The proposed connection can knight is new and acetylene hydrocarbons, as well as in thin organic and ORGANOMETALLIC synthesis.

The known method ([1], RF Patent 2157812, CL 07 F 7/2, 5/6) obtaining substituted five-membered cyclic AOC, namely, 1-ethyl-3(trialkylsilyl)almacenamento (2) interaction trialkylsilanes with triethylaluminium (AlEt3in the presence of a catalyst Cp2ZrCl2taken in a molar ratio trialkylindium: AlEt3:Cf2ZrCl2=10:15:0,5, at a temperature of 21-22oWith over 6-10 hours scheme

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R=Me, Et, n-Bu.

The known method does not allow to obtain unsaturated almacenamento (1).

The known method ([2] , Dzhemilev, U. M., A. G. Ibragimov, Zolotarev A. P. Synthesis of 1-Ethyl-cis-2,3-dialkyl(aryl)aluminacyclopent-2-enes. A Novel Class of Five - membered Organoaluminum Compounds. Mendeleev Commun., 1992, 4, p.135) obtain unsaturated five-membered cyclic AOC, namely, 1-ethyl-2,3-dialkylanilines-2-ENES (3) the interaction of dialkylanilines with triethylaluminium taken in a molar ratio of 1:2.5 in the presence of 3-5 mol. % Cp2ZrCl2at a temperature of 23-25oC for 10-12 h scheme

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The known method does not allow to obtain the substituted 1-ethylaminomethyl (1).

Thus, in the literature there are no data on the selective synthesis is acyclovirtab (1).

The method consists in the interaction of substituted allenes General formula R-==, where R=n-C6H13n-C8H17Ph, triethylaluminium (Et3Al), taken in a molar ratio R-==:Et3Al=10:(10-14), preferably 10:12, in the presence of a catalyst of zirconatetitanate (Cp2ZrCl2) in an amount of 2-6 mol. % relative to the 1-substituted Allen, preferably 4 mol.%, in an argon atmosphere at room temperature (~20oC) and normal pressure in methylene chloride (CH2CL2) as solvent. The reaction time is 8-12 hours, preferably 10 hours. The total yield of substituted 1-ethylaminoethanol (1) is 82-96%.

The reaction proceeds according to the scheme

< / BR>
R=n-C6H13; n8H17, PH.

Substituted 1-ethylaminomethyl (1) are formed only with the participation of Et3Al and zirconium catalyst Cp2ZrCl2. In the presence of other aluminum compounds (e.g., Bu2iAlCl, VI3iAl, Bu2iAlH, EtAlCl2Et2AlCl) or other catalysts (e.g., Zr(acac)4, ZrCl4Cp2TiCl2Pd(acac)2, Ni(acac)2, NiCl2, Fe(acac)2target products (1) are not formed.

oC. At a higher temperature (e.g., ~40o(C) has not been a significant increase in the yield of the target product, and at a lower temperature (for example, 0oC) decreases the reaction rate.

Changing the ratio of initial reagents in the direction of increasing the content of Et3Al in relation to the original 1-substituted Allen does not lead to a significant increase in the yield of target products (1).

The reaction was performed using methylene chloride as solvent. In other solvents (for example, aliphatic or aromatic) decreases the regiospecificity of the reaction along with substituted 1-ethylaminoethanol (1) observed the formation of significant amounts of 1-ethyl-2-methylene-3-alkylarylsulfonates.

Significant differences of the proposed method:

In the proposed method are used as a source of unsaturated compounds substituted alley that lead to the formation of substituted 1-ethylaminoethanol (1). In Izvestkovaya the formation of 1-ethyl-2,3-dialkylanilines-2-ENES (3).

The proposed method has the following advantages:

1. The method allows to obtain high selectivity of substituted 1-ethylaminomethyl (1), the synthesis of which are not described in literature.

The method is illustrated by the following examples:

Example 1. In a glass reactor with a volume of 50 ml, mounted on a magnetic stirrer, an argon atmosphere was placed 5 ml of methylene chloride (CH2CL2), 10 mmol of 1,2-nonadiene, 0.4 mmol Cp2ZrCl2at a temperature of ~0oWith 12 mmol Et3Al, stirred for 10 hours at room temperature (~20oC). Get 1-ethyl-2-getelementattributes (1) with the release of 88%.

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An NMR spectrum13With (, m D.) 1-ethyl-2-getelementopentype (1): 18,10 ush. C. (WITH1), 33,41 t (2), 34,88 t (3), 170,40 ush.with. (WITH4), 146,53 d (5), 25,45 t (6), 28,77 t (7), to 29.61 t (8), 32,18 t (9), of 23.11 t (10), 14,33 to (11), 0,81 t (12), compared to 8.26 (WITH13).

Other examples of the method shown in the table.

The reaction was carried out at room temperature (-20o(C) in methylene chloride.

The method of obtaining substituted 1-ethylaminoethanol General formula (1)

< / BR>
where R=n-C63Al in a molar ratio R-= = : Et3Al=10:(10-14), respectively, in the presence of a catalyst of zirconatetitanate (Cf2ZrCl2) in an amount of 2-6 mol % relative to the substituted Allen and the reaction is performed in the environment of methylene chloride in an argon atmosphere at room temperature for 20oC and normal pressure for 8-12 hours

 

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