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Method for realizing coupling of disubstituted amide and diphenylketone
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A benzophenone and disubstituted technology, applied in the field of organic chemical synthesis, achieves the effects of fewer operation steps, lower reaction costs, and simplified operation requirements
Active Publication Date: 2018-12-14
QINGDAO UNIV OF SCI & TECH
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[0006] The invention discloses a method for promoting the condensation coupling reaction of diphenyl ketone and N,N-disubstituted amide under the catalysis of cuprous iodide by using samarium metal in a small amount of N,N-disubstituted amide. There are no domestic and foreign literature reports
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example 1
[0018] Add 3.6g of benzophenone and 5mL of N,N-dimethylacetamide to the dry reaction vessel in sequence, stir and dissolve, then add 0.9g of fresh samarium metal powder, 5mg of iodine and 2.6mg of Cuprous iodide, magnetic stirring. The reaction was carried out at 80°C for 2h. The reaction solution was extracted with ethyl acetate and processed to obtain a crude product. Then it was further separated by column chromatography and purified by recrystallization to obtain 3,3-diphenyl-3-hydroxy-N,N-dimethylpropanamide with a yield of 86%.
[0019] 3,3-Diphenyl-3-hydroxy-N,N-dimethylpropionamide, white solid, melting point 105-106℃. 1 HNMR (500MHz, CDCl 3 )δppm 2.87-2.90(s,3H),3.00-3.04(s,3H),3.20-3.24(s,2H),6.67-6.70(s,1H),7.19-7.23(t,2H),7.28-7.33 (m,4H),7.37-7.43(d,4H).
example 2
[0021] According to the method of example 1, replace N,N-dimethylacetamide with N,N-dimethylpropionamide, and other conditions remain unchanged, to obtain 3,3-diphenyl-3-methyl-3-hydroxyl- N,N-Dimethylpropanamide, yield 87%.
[0024] According to the method of Example 1, using 1.5 g of freshly prepared samarium powder and other conditions unchanged, 3,3-diphenyl-3-hydroxy-N,N-dimethylpropionamide was obtained with a yield of 91%.
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Abstract
The invention discloses a method for realizing condensation coupling of diphenylketone and N,N-disubstituted amide under the catalysis of cuprous iodide and the promotion of metalsamarium. The diphenylketone is mixed and dissolved into a small amount of N,N-disubstituted amide under stirring, and metalsamariumpowder, iodine with the catalysis quantity and cuprous iodidepowder. The reaction system is conducted under the waterless condition. The reaction temperature range is from room temperature to reflux temperature. Stirring is conducted until complete reaction. The obtained reaction mixed liquid is subjected to after treatment and the pure product is obtained through chromatographic column separation, and the yield is 60 to 95 percent.
Description
technical field [0001] The invention belongs to the field of organic chemical synthesis, and in particular relates to a condensation coupling method of N,N-disubstituted amides and diphenyl ketone promoted by metalsamarium under the condition of no solvent. Background technique [0002] The carbanion condensation coupling reaction is one of the basic reaction strategies to build carbon-carbon bonds in organic synthesis, such as the aldol condensation reaction [Document 1. Pu, et al. Catalytic aldol condensation method of aldehydes, CN201380062177.8, 2013.11], and condensation coupling reactions of carboxylic acid derivatives and carbonyl compounds such as ketones, etc. Among them, the classic Claisen ketone ester condensation reaction, triethyl synthesis method and malonate synthesis method, Perkin condensation reaction, Knoevenagel condensation reaction, etc., all belong to the condensation coupling between carboxylic acid derivatives and carbonyl compounds such as aldehyd...
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