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A method for preparing α-alkyl-β-keto esters
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A compound and alkyl technology, which is applied in the field of preparation of α-alkyl-β keto ester compounds, can solve the problem of low reduction yield and achieve the effect of rich variety, simple operation and excellent industrial application prospect
Active Publication Date: 2020-08-21
XIHUA UNIV
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However, the reaction reduction yield is very low, only 35%
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Embodiment 1
[0035] Embodiment 1 The inventive method is to the screening of catalyst
[0036] The reaction equation is as follows:
[0037]
[0038] Add ethyl 2-benzoyl-3-phenylacrylate (28mg, 0.1mmol) into the reaction flask, then add dihydropyridinate (30.36mg, 0.12mmol), catalyst (0.02mmol), 1.5ml of water, and stir Mix well and react at 100°C for 24 hours. After the reaction is complete, extract with ethyl acetate and perform silica gelcolumn chromatography (PE:EA=10:1) to obtain a light yellow liquid. The yield is shown in Table 1.
[0039] Table 1 Screening of different catalysts
[0040]
[0041] The results show that the catalysts Cat 3, Cat 4, Cat 5, Cat 6 and Cat 7 are more effective.
Embodiment 2
[0042] Embodiment 2 The influence of the inventive method on reaction temperature, time and solvent consumption
[0043] The reaction equation is as follows:
[0044]
[0045] Add ethyl 2-benzoyl-3-phenylacrylate (28mg, 0.1mmol) into the reaction flask, then add dihydropyridinate (30.36mg, 0.12mmol), catalyst Cat 5 (9.7mg, 0.02mmol), Water (0.5-5mL), stirred and mixed, reacted at different temperatures (≤100°C) for 8-24 hours, after the reaction was complete, extracted with ethyl acetate and removed the solvent under reduced pressure, silica gelcolumn chromatography (PE: EA=10:1), a light yellow liquid was obtained, and the yields are shown in Table 2.
[0048] The results show that when the reaction temperature is 90-100° C., the reaction time is 24 hours, and the volume molar ratio of the solvent to the reaction raw material 2-benzoyl-3-phenylacrylate ethyl ester is (5-50) L: 1...
Embodiment 3
[0050] The reaction equation is as follows:
[0051]
[0052] Add ethyl 2-benzoyl-3-phenylacrylate (28mg, 0.1mmol) into the reaction flask, then add dihydropyridinate (30.36mg, 0.12mmol), catalyst Cat 5 (9.7mg, 0.02mmol), 1.5ml of water, stirred and mixed, reacted at 100°C for 24 hours, after the reaction was complete, extracted with ethyl acetate, distilled under reduced pressure, and silica gelcolumn chromatography (PE:EA=10:1) to obtain light yellow oil Viscous liquid, yield 93%.
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Abstract
The invention discloses a method for preparing an alpha-alkyl-beta-ketone ester compound shown as a formula (I). The method comprises the following steps: a 1,4-dihydropyridine ester compound shown asa formua (III) is taken as a reducing agent, and under existence of a Lewis acid catalyst, a compound in a formula (II) is subjected to a reduction reaction to obtain the alpha-alkyl-beta-ketone ester compound shown as the formula (I). The method has the advantages of simple operation, mild condition and environmental protection, and is suitable for a plurality of substrates, and the yield can reach as highest as 95%. By using the method of the invention, a plurality of alpha-alkyl-beta-ketone ester compounds can be efficiently prepared, types of medical intermediates are enriched, and the method has an excellent industrial application prospect.
Description
technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for preparing an α-alkyl-β keto ester compound. Background technique [0002] α-Alkyl-β-keto esters are a very important class of pharmaceutical intermediates. Many natural products and biologically active heterocyclic substances can be derived from them, and their applications are very extensive. In recent years, there are roughly three types of preparation methods for α-alkyl-β-keto esters reported in the literature: synthesis by Heck and Heck-like reactions of Baylis-Hillman products; preparation by Roskamp reaction; preparation by substitution reaction of halogenated hydrocarbons . However, these methods have disadvantages such as rare raw materials, expensive catalysts, and the need for organic solvents. [0003] The literature Catalyst-free chemoselective reduction of the carbon–carbon double bond in conjugated alkenes with Hantzsch esters in water (RSC Adv., 201...
Claims
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