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A kind of synthetic method of 1,2,3-triphenylpropan-1-one
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A synthetic method, triphenyl technology, applied in 1 field, can solve problems such as reaction efficiency problems, and achieve the effects of easy handling, improved reaction efficiency, and shortened reaction time
Active Publication Date: 2020-07-31
ZHENGZHOU UNIV
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Problems solved by technology
Various transition metal complexes (Ir, Rh, Ru, Pd, Cu, Os, etc.) have been developed for heterogeneous and heterogeneous BH catalysis, but there are still problems of reaction efficiency
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Embodiment 1
[0020] In a 15ml Schlenk tube, add 78.5 mg (0.4 mmol) diphenyl ethyl ketone, 47.6 mg (0.44 mmol) benzyl alcohol, 26.63 mg (0.25 equiv) potassium phosphate trihydrate, 0.5 ml tert-amyl alcohol, and magnetically stir under an argon atmosphere , and reacted for 12 h at 120°C. Through TLC analysis, the product content Trace.
Embodiment 2
[0022] The synthetic method of 1,2,3-triphenylpropan-1-one of the present embodiment, the steps are as follows:
[0023] In a 15 ml Schlenk tube, add 78.5 mg (0.4 mmol) diphenylethanone, 47.6 mg (0.44 mmol) benzyl alcohol, 1.55 mg (0.5 mol%) pincer metal ruthenium(II) compound, 26.63 mg (0.25 equiv ) Potassium phosphate trihydrate, 0.5 ml tert-amyl alcohol, magnetically stirred under an argon atmosphere, and reacted at 120°C for 12 h. Through TLC analysis, the raw material diphenyl ethyl ketone has reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 1,2,3-triphenylpropan-1-one has a mass of 88.20 mg and a yield of 77%. product by 1 H NMR, 13 Confirmed by C NMR. 1 H NMR (400MHz, CDCl 3 ) δ 7.89 (d, J = 7.6, 2H), 7.43-7.39 (m, 1H), 7.31 (t, J = 7.6 Hz, 2H), 7.24-7.07(m, 10H), 4.81 (t, J = 7.2 Hz, 2H), 3.56 (dd, J = 7.6 Hz, 13.6 Hz,1H). 3.06(dd, J = 6.8 Hz, 13.8 Hz,1H). 13 C NMR (100 MHz, CDCl 3 ) ...
Embodiment 3
[0025] The synthetic method of 1,2,3-triphenylpropan-1-one of the present embodiment, the steps are as follows:
[0026] In a 15 ml Schlenk tube, add 78.5 mg (0.4 mmol) diphenylethanone, 43.3 mg (0.4 mmol) benzyl alcohol, 1.55 mg (0.5 mol%) pincer metal ruthenium(II) compound, 10.8 mg (0.5 equiv ) sodium methoxide, 0.5ml of a mixed solution of dichloromethane and toluene, magnetically stirred under an argon atmosphere, and reacted at 120°C for 12 h. Through TLC analysis, the raw material diphenyl ethyl ketone has reacted completely. Vacuum rotary evaporation, separation and purification by thin layer chromatography, the product 1,2,3-triphenylpropan-1-one was 85.17 mg, and the yield was 78%.
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Abstract
The invention discloses a method for synthesizing 1,2,3-triphenylpropan-1-one. The method comprises the following steps: adding phenylacetophenone, benzyl alcohol, a catalyst, an alkaline and a solvent into a reactor in sequence; performing magnetic stirring and reacting in an argon atmosphere; fully reacting in an oil bath pan; after the reaction is ended, performing vacuum rotating evaporation,chromatography separation and drying to obtain a target product. According to the method, the problem of a large amount of by-products caused by using reagents in a conventional synthesizing method isavoided, because the reagents are cheap, easy to store and environmentally friendly, and are renewable alternative petroleum base compounds. In the method, a NNN-type pincerlike metal ruthenium (II)compound is adopted as a catalyst of a catalytic reaction; the reaction is completed by one step; the operation is simple and convenient; the reaction efficiency is high; the requirement on sustainable development of green chemistry is met.
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 1,2,3-triphenylpropan-1-one. Background technique [0002] The ability to manipulate and extend carbon functionality through carbon-carbon bond-forming reactions is crucial for synthetic organic chemistry, such as medicinal chemistry, pesticides, and natural product synthesis. In this case, aldehydes and ketones play a key role because their carbonyl functionality can participate in an array of reactions leading to carbon-carbon bond formation, such as organometallic reagents (organolithium, Grignard reagents, etc.), cyanide, Attack of various carbonyl nucleophiles such as enolates derived from active methylene compounds, and preparation by Wittig-type reagents. Furthermore, these compounds can also act as C-nucleophiles via the corresponding enols, eg in aldol reactions. In recent years, the use of alcohols as starting materials for ...
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