A kind of preparation method of cyclohexane triketone compound
A technology of cyclohexanetrione and compound, which is applied in the field of preparation of organic compounds, can solve the problems of increased process cost, difficulty in post-processing, pressure on environmental protection, etc., and achieves the effects of fast reaction, less three wastes, and simple post-processing
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[0011] The steps of the preparation method of cyclohexanetriketone compound are as follows:
[0012] In the first step, enol ester is used as raw material, and azide quaternary ammonium salt is added under the condition of 25-60°C, and the mass ratio of azide quaternary ammonium salt to enol ester is 0.01-0.5;
[0013] In the second step, organic amine is added, and the molar ratio of organic amine to enol ester is 1.0 to 5.0;
[0014] The third step is to stir until the reaction is complete to obtain cyclohexanetrione compounds.
[0015] The cyclohexane triketone compounds are: ethyl 4-cyclopropylformyl-3,5-diketone cyclohexanecarboxylate, ethyl 4-propionyl-3,5-diketone cyclohexanecarboxylate ester. The azide quaternary ammonium salt is: one or more of tetrabutyl ammonium azide, tetraethyl ammonium azide, tetrapropyl ammonium azide or benzyl triethyl ammonium azide mixture. The organic amine is: one or more mixtures of triethylamine, tributylamine, benzyldiethylamine or i...
Embodiment 1:106.0g 5--4--3-、53.0g 3 and 5.3g 4 1000mL,25℃ to 。300mL and ,pH=3, to 104.0g4-()-3,5- 2 ,98.0%。4-()-3,5- 2 :1HNMR(500MHz,CDCl3):δ4.17~4.21(q,2H),3.53~3.58(m,1H),3.04~3.10(m,1H),2.87~2.96(m,2H),2.78~2.85(m,1H),2.69~2.74(m,1H),1.26~1.32(m,5H),1.13~1.16(m,1H)。 Embodiment 2
[0017] Example 1: Add 106.0g ethyl 5-cyclopropylformyloxy-4-cyclohexen-3-onecarboxylate, 53.0g triethylamine and 5.3g tetra-n-butylammonium azide to 1000mL for reaction In the bottle, stir at 25°C until the reaction is complete. Add 300mL of a mixture of chloroform and water, adjust the pH to 3 with hydrochloric acid, and desolventize the organic layer to obtain 104.0g of ethyl 4-cyclopropyl(hydroxy)methylene-3,5-diketonecyclohexanecarboxylate. The rate is 98.0%. The nuclear magnetic resonance spectrum data of described 4-cyclopropyl (hydroxyl) methylene-3,5-diketone cyclohexanecarboxylate ethyl ester compound is as follows: 1 HNMR (500MHz, CDCl 3 ): δ4.17~4.21(q,2H), 3.53~3.58(m,1H), 3.04~3.10(m,1H), 2.87~2.96(m,2H), 2.78~2.85(m,1H), 2.69 ~2.74(m, 1H), 1.26~1.32(m, 5H), 1.13~1.16(m, 1H). Example 2: Add 40.0g ethyl 5-acetoxy-4-cyclohexen-3-onecarboxylate, 26.5g benzyldiethylamine and 1.2g benzyltriethylammonium azide to 500mL reaction In the bottle, stir at 60°C until the...
Embodiment 3
[0018] Example 3: Add 53.0g ethyl 5-cyclopropylformyloxy-4-cyclohexen-3-onecarboxylate, 26.5g tributylamine and 2.7g tetraethylammonium azide into a 500mL reaction flask , Stir at 25°C until the reaction is complete. Add 250 mL of a mixture of toluene and water, adjust the pH to 5 with hydrochloric acid, and obtain 50.4 g of ethyl 4-cyclopropyl(hydroxy)methylene-3,5-diketonecyclohexanecarboxylate through precipitation of the organic layer. Yield 95.1%.
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