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Method for direct alpha-hydroxylation by beta-dicarbonyl compound under action of iodine catalysis

A dicarbonyl compound and hydroxylation technology is applied in the field of direct α-position hydroxylation of β-dicarbonyl compounds catalyzed by iodine, which can solve the problems of harsh reaction conditions, complicated operations, expensive catalysts, etc., and achieves simple product separation and extended application range. , to achieve the effect of simplicity

Inactive Publication Date: 2012-10-03
CHANGZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] The present invention provides a simple and efficient method for catalyzing the α-hydroxylation of β-dicarbonyl compounds in order to overcome the shortcomings of complex operation, harsh reaction conditions and expensive catalysts in the prior art

Method used

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  • Method for direct alpha-hydroxylation by beta-dicarbonyl compound under action of iodine catalysis
  • Method for direct alpha-hydroxylation by beta-dicarbonyl compound under action of iodine catalysis
  • Method for direct alpha-hydroxylation by beta-dicarbonyl compound under action of iodine catalysis

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Weigh 7 (1mmol), I in "Reaction Formula 3" 2 (25.6mg, 0.01mmol) and NaOAc (4.1mg, 0.01mmol) in a 25mL round-bottomed flask, then add 10mL THF at 25°C and place it in the air and stir. The reaction was tracked by TLC. After the raw materials disappeared, most of the solvent was removed from the reactant on a rotary evaporator, and 40 mL of water and saturated Na were added. 2 S 2 O 3 Solution until the color of iodine disappears. Extracted with dichloromethane (15mL×3), the organic layer was subjected to anhydrous MgSO 4 After drying, the mixture obtained by rotary evaporation is separated by silica gel column chromatography (the eluent is petroleum ether / ethyl acetate: v / v=6 / 1). The main component obtained is product 8, and the yield is 90%.

Embodiment 2

[0040] Weigh 7 (1mmol), I in "Reaction Formula 3" 2 (128mg, 0.5mmol) and NaOAc (41mg, 0.5mmol) in a 25mL round-bottomed flask, and then add 10mL THF at 25°C and place it in the air and stir. The reaction was tracked by TLC. After the raw materials disappeared, most of the solvent was removed from the reactant on a rotary evaporator, and 40 mL of water and saturated Na were added. 2 S 2 O 3 Solution until the color of iodine disappears. Extracted with dichloromethane (15mL×3), the organic layer was subjected to anhydrous MgSO 4 After drying, the mixture obtained by rotary evaporation is separated by silica gel column chromatography (the eluent is petroleum ether / ethyl acetate: v / v=6 / 1). The main component obtained is product 8, and the yield is 95%.

Embodiment 3

[0042] Weigh 7 (1mmol), I in "Reaction Formula 3" 2 (25.6mg, 0.1mmol) and NaOAc (17mg, 0.1mmol) in a 25mL round-bottomed flask, and then add 10mL THF at 25°C and place it in the air and stir. The reaction was tracked by TLC. After the raw materials disappeared, most of the solvent was removed from the reactants on a rotary evaporator, and 40 mL of water and saturated Na2S were added. 2 O 3 Solution until the color of iodine disappears. Extracted with dichloromethane (15mL×3), the organic layer was subjected to anhydrous MgSO 4 After drying, the mixture obtained by rotary evaporation is separated by silica gel column chromatography (the eluent is petroleum ether / ethyl acetate: v / v=6 / 1). The main component obtained is product 8, and the yield is 93%.

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Abstract

The invention relates to the field of organic chemical industry, in particular to a method for direct alpha-hydroxylation by a beta-dicarbonyl compound under the action of iodine catalysis. The beta-dicarbonyl compound with different substituents is taken as a raw material to synthetize alpha-hydroxy product under the action of iodine catalysis; the method is characterized in that iodine is taken as a catalyst, wherein an alkali used is carbonate or acetate or organic carboxylate, THF (tetrahydrofuran) is used as a solvent, and the reaction conditions are specified as follows: the reaction time is 8-24 hours and the amount of the used catalyst I2 is 1 to50 percent of the beta-dicarbonyl compound under the condition of stirring at the temperature of 0-60 DEG C. Compared with the preparation method in the document, the method provided by the invention has the advantages of low toxicity in raw materials, mild reaction conditions, short reaction time, low price and easily availability of the catalyst, convenience in separation and purification and the like, thereby having a very high application value.

Description

Technical field [0001] The invention relates to the field of organic chemical engineering, in particular to a method for iodine-catalyzed direct α-position hydroxylation of β-dicarbonyl compounds. Background technique [0002] Among the many acid catalysts, proton acid catalyzed organic reactions have the disadvantages of many side reactions, complex post-treatment processes, serious corrosion to reaction equipment, and serious environmental pollution. However, some solid acid and lewis acid catalysts have insufficient raw materials, low catalytic efficiency, and high reaction temperature. Therefore, it is necessary to find low-cost, high-efficiency and mild reaction conditions. In recent years, as a mild lewis acid catalyst, iodine has been widely used in the field of catalytic organic synthesis. This type of reaction has mild conditions, easy operation, high reaction yield or high selectivity, stable reaction process, environmental friendliness, and raw material price The adva...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C67/31C07C69/732C07C69/738C07C231/12C07C235/34C07C69/757C07C227/16C07C229/24
Inventor 董春萍缪春宝王艳红杨海涛孙小强
Owner CHANGZHOU UNIV
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