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Method for deoxidizing and reducing aldehyde ketone into corresponding saturated hydrocarbon
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An aldehyde and ketone reaction technology, applied in the field of saturated hydrocarbon synthesis, can solve the problems of hydrogen flammability, high reaction temperature, and great safety hazards.
Pending Publication Date: 2022-04-26
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE +1
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[0006] Disadvantages: This method requires the use of highly toxic zinc amalgam, which will cause serious mercury pollution to the environment; and with the increasing shortage of mercury sources in recent years, the cost is getting higher and higher;
[0009] Disadvantages: This method has a high reaction temperature (200°C) and requires a large amount of strong base action, so many substrates sensitive to alkali and high temperature are limited; in addition, this method uses a large amount of hydrazine, and the atom utilization rate is low
[0012] Disadvantages: Generally speaking, the use of Pd / C to catalyze hydrogenation reduction has special requirements for the substrate. Generally, the substrate is required to be arylalkyl ketone or diaryl ketone; in addition, there are unsaturated carbon-carbon double Neither the bond nor the triple bond can be retained; Raney nickel is extremely flammable when exposed to air; and hydrogen is also extremely flammable, and flash explosion may occur when the concentration in the air reaches an extreme value
Therefore, although the cost of this method is low, there is a large potential safety hazard.
[0013] In summary, the existing methods for deoxygenating aldehydes and ketones to corresponding saturated hydrocarbons have obvious deficiencies and need to be improved.
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Embodiment 1
[0023]
[0024] Take benzophenone (182.0 mg, 1.0 mmol, 1.0eq.), NaCl (116.9 mg, 2.0 mmol, 2.0 eq.) In a 10 mL three-necked bottle; add CH 3 CN(8.0mL)，H 2 O (1.0 mL), stirred to dissolve; hydrochloric acid (HCl, 36%, 0.52 mL, 6.0eq.), formic acid (HCOOH, 0.18 mL, 6.0eq.) was added. Insert electrodes (anodezinc rod or zinc sheet, cathodegraphite felt) in a three-necked bottle, energize, 30 mA constant current reaction for about 1 h. After the reaction is complete, the solvent is recovered by distillation and H is added 2O (10 mL), extracted with DCM (3×5 mL), combined organic phase, anhydroussodiumsulfate dried, filtered, distilled out of the recovered solvent residue by column chromatography to obtain the product, yield 81%.
Embodiment 2
[0026]
[0027] Take benzophenone (182.0 mg, 1.0 mmol, 1.0eq.), NaCl (5.8 mg, 0.1 mmol, 0.1 eq.) In a 10 mL three-necked bottle; add CH 3 CN(8.0mL)，H 2 O (1.0 mL), stirring to dissolve; hydrochloric acid (HCl, 36%, 0.52 mL, 6.0eq.), formic acid (HCOOH, 0.18 mL, 6.0 eq.) was added. Insert electrodes (anode zinc rod or zinc sheet, cathodegraphite felt) in a three-necked bottle, energize, 30mA constant current reaction for about 1h. After the reaction is complete, the solvent is recovered by distillation and H is added 2 O (10 mL), extracted with DCM (3 ×5 mL), combined organic phase, anhydroussodiumsulfate dried, filtered, distilled out of the residue after recovery of the solvent was separated by column chromatography to obtain the product, the yield was 30%.
Embodiment 3
[0029]
[0030] Take benzophenone (182.0 mg, 1.0 mmol, 1.0eq.), NaCl (584.4 mg, 10.0 mmol, 10.0 eq.) In a 10 mL three-necked bottle; add CH 3 CN(8.0mL)，H 2 O (1.0 mL), stirred to dissolve; hydrochloric acid (HCl, 36%, 0.52 mL, 6.0eq.), formic acid (HCOOH, 0.18 mL, 6.0eq.) was added. Insert electrodes (anode zinc rod or zinc sheet, cathodegraphite felt) in a three-necked bottle, energize, 30 mA constant current reaction for about 1 h. After the reaction is complete, the solvent is recovered by distillation and H is added 2 O (10 mL), extracted with DCM (3×5 mL), combined organic phase, anhydroussodiumsulfate dried, filtered, distilled to recover the solvent residue by column chromatography to obtain the product, yield 91%.
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Abstract
The invention discloses a synthesis method for deoxidizing and reducing an aldehydeketone compound into a corresponding saturated hydrocarbon compound under an electrochemical condition, and relates to the technical field of medicine and material synthesis. The synthesis method comprises the following steps: dissolving aldehydeketone, electrolyte and protonic acid in a solvent in an electrochemical reaction tank, connecting an electrode, and carrying out electrifying reaction at room temperature, so as to reduce the aldehydeketone compound into the corresponding saturated hydrocarbon compound. The method can be widely applied to large-scale synthesis of corresponding medicines, intermediates and materials.
Description
Technical field [0001] The present invention relates to the field of pharmaceutical and material synthesis technology, in particular to a synthetic method for deoxygenated aldehydes and ketones as corresponding saturated hydrocarbons under electrochemical conditions. Background [0002] In the history of drug synthesis, the green and efficient reduction of aldehyde and ketone compounds to their corresponding saturated hydrocarbons is a synthesis method with extremely high value, which is widely used in the synthesis of a large number of drugs. [0003] According to the literature, there are several methods for reducing aldehyde and ketone deoxygenation to saturated hydrocarbons as follows: [0004] (1) Clemmensen restore [0005] [0006] Disadvantages: This method requires the use of highly toxic zinc amalgam, which can cause serious mercury pollution to the environment; and with the increasing tension of mercury sources in recent years, the cost is getting higher and higher;...
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