Preparation method of b-heterocyclic ketone compound
A technology of ketone compounds and compounds, which is applied in the field of preparation of β-heterocyclic substituted ketone compounds, can solve the problems of large industrial wastewater, complicated operation, high production cost, etc., and achieve high reaction yield, safe and convenient operation, and mild reaction conditions Effect
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[0027] Example 1
[0028] The preparation of 4-(2-5-methoxythiophene)-non-2-one: the ratio of the amount of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0:2.0:0.1, and the hetero The cyclic compound is 2-methoxythiophene, the catalyst is palladium dichloride, the organic solvent is tetrahydrofuran, and the amount is 10 times that of 3-nonen-2-one. Add 70.1 mg (0.5 mmol) of 3-nonen-2-one, 114.2 mg (1.0 mmol) of 2-methoxythiophene, and 8.8 mg (0.05 mmol) of palladium dichloride into a 25 mL Schlinker flask containing magnets. ), 1.0 mL of tetrahydrofuran, stirred for reaction at 0°C, the reaction was complete after 0.25h. After the reaction was completed, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain the 4-(2-5-methoxythiophene)-nonane -2-ketone liquid, pure product 123.4mg, yield 97%.
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[0029] Example 2
[0030] The preparation of 4-(2-5-methylfuran)-non-2-one: the ratio of the amount of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0:3.0:0.1, wherein the heterocyclic ring The compound is 2-methylfuran, the catalyst is palladium acetate, the organic solvent is n-hexane, and the amount is 60 times that of 3-nonen-2-one. Add 70.1mg (0.5mmol) of 3-nonen-2-one, 123.1mg (1.5mmol) of 2-methylfuran, 11.2mg (0.05mmol) of palladium acetate, The alkane was 5.0 mL, and the reaction was stirred at 60° C. The reaction was complete after 10 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1)) to obtain the 4-(2-5-methylfuran)-non- 2-ketone liquid, pure product 108.9mg, yield 98%.
Example Embodiment
[0031] Example 3
[0032] The preparation of 4-(3-N-methylindole)-non-2-one: the ratio of the amount of feed material is 3-nonen-2-one: heterocyclic compound: catalyst is 1.0:1.0:0.1, and the hetero The cyclic compound is N-methylindole, the catalyst is bis(acetonitrile) palladium dichloride, the organic solvent is n-butanol, and the amount is 100 times that of 3-nonen-2-one. Add 70.1 mg (0.5 mmol) of 3-nonen-2-one, 65.6 mg (0.5 mmol) of N-methylindole, and 13.0 bis(acetonitrile) palladium dichloride into a 25 mL Schlinker flask containing a magnet mg (0.05 mmol), 9.0 mL of n-butanol, stirred for reaction at 130°C, and the reaction was complete after 48 hours. After the reaction was completed, the solvent was removed under reduced pressure, and the product was separated and purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain the 4-(3-N-methylindole)-nonane -2-ketone liquid, pure product 115.3mg, yield 85%.
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