A kind of preparation method of cyclopentenyl aryl ketoxime compound
A technology for cyclopentenyl aryl ketoxime and compound, which is applied in the field of preparation of cyclopentenyl aryl ketoxime compounds and achieves the effect of mild reaction conditions
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[0029] The synthesis method of compound I refers to the following literature: Pin Gao, Xiao-Biao Yan, Tao Tao, Fan Yang, Ting He, Xian-Rong Song, Xue-Yuan Liu, and Yong-Min Liang, Chem.Eur.J.,2013 , 19, 14420-14424. Specific steps are as follows:
[0030] Will K 2 CO 3 (13.8g, 100mmol, 1.0eq), 3-bromo-2-methylpropene (14.9g, 100mmol, 1.0eq) were successively added to an acetone solution of diethyl malonate (17.2g, 130mmol, 1.3eq) ( 120mL). The mixture was stirred at room temperature for 24 hours. filter through funnel to remove K 2 CO 3 . The resulting mixture was extracted with dichloromethane (3*80 mL), washed with saturated brine solution, and dried over sodium sulfate. The residue was further purified by flash column chromatography to obtain the desired product, diethyl 2-(2-methallyl)malonate, in a yield of 76% (petroleum ether / ethyl acetate=200:1).
[0031] Will K 2 CO 3 (13.8g, 100mmol, 2.0eq), 3-bromopropyne (10.5g, 100mmol, 2.0eq) were added to 2-(2-methall...
Embodiment 1
[0034] Embodiment 1: General structural formula I, wherein R 1 for hydrogen, R 2 and R 2' is the preparation method of ethyl cyclohexenyl aryl ketone oxime.
[0035] In a 20 mL dry reaction tube, under a nitrogen atmosphere, the raw materials 2-methallyl-2-aryl propargyl malonate (0.164 g, 0.5 mmol), tert-butyl nitrite ( 0.103g, 1mmol), polymethylsiloxane (0.333g, 1.5mmol), iron catalyst Fe(acac) 3 (35.32mg, 0.1mmol), 10mL tetrahydrofuran, and the mixed system was reacted at 60°C for 24 hours. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography to obtain a high-purity ketoxime product (yellow oil, 0.10 g, yield 56%). From the proton nu...
Embodiment 2
[0037] Embodiment 2: general structural formula I, wherein R 1 is 4-methyl, R 2 and R 2 ' is the preparation method of ethyl cyclohexenyl aryl ketone oxime.
[0038] In a 20 mL dry reaction tube, under a nitrogen atmosphere, the raw materials 2-methallyl-2-aryl propargyl malonate (0.171 g, 0.5 mmol), tert-butyl nitrite ( 0.103g, 1mmol), polymethylsiloxane (0.333g, 1.5mmol), iron catalyst Fe(acac) 3 (35.32mg, 0.1mmol), 10mL tetrahydrofuran, and the mixed system was reacted at 60°C for 24 hours. As detected by TLC, the raw material disappeared, and the reaction was completed, and quenched by adding water. The aqueous phase was extracted twice with ethyl acetate (20 mL×2), the combined organic phases were washed once with saturated brine, and the solvent was removed by spinning under reduced pressure to obtain a crude product. The crude product was subjected to column chromatography to obtain a high-purity ketoxime product (yellow solid, melting point 119-121° C., 0.11 g, yi...
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