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Novel synthesis method for three-stage alpha-hydroxyl carbonyl compound

A synthesis method and compound technology, applied in the field of organic chemical synthesis, can solve the problems of increased production cost, insufficient environmental protection, unsuitable for large-scale production, etc., achieving the effects of abundant sources and overcoming low reaction yields

Inactive Publication Date: 2014-07-02
CHINA UNIV OF GEOSCIENCES (BEIJING)
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Although there are many α-hydroxylation synthesis processes of carbonyl compounds in the prior art, some of these methods do not use natural molecular oxygen as an oxidant source, which is not environmentally friendly, and some methods use expensive rare metal catalysts or complex polymer catalysts, which greatly increase the production cost of enterprises
The existence of these problems makes the current technology unsuitable for large-scale production in the field of chemical and pharmaceutical intermediate synthesis.

Method used

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  • Novel synthesis method for three-stage alpha-hydroxyl carbonyl compound
  • Novel synthesis method for three-stage alpha-hydroxyl carbonyl compound
  • Novel synthesis method for three-stage alpha-hydroxyl carbonyl compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]

[0035] Add 1 mol formula (I) compound, 2.05 mol sodium carbonate and 1.9 mol isopropyltriphenylphosphine bromide successively in the reactor at room temperature, and keep stirring under oxygen atmosphere, then add 8L DMSO and mass ratio thereto 1:0.7:0.5 of N,N-diisopropylethylamine (DIPEA), SmI 2 and a mixture additive of ferrocene (total mass is 2000g), the mixture is continuously stirred under an oxygen atmosphere at room temperature, and reacted for a total of 18h. After the reaction is completed, ethyl acetate is added for dilution, followed by washing with salt water and extraction with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified by column chromatography to obtain the compound of formula (II) with a yield of 97.5% and a purity of 98.7% (HPLC).

[0036] 1 H NMR (400MHz, CDCl 3)δ=7.46-7.41(m,2H),7.23(t,J=7.6Hz,1H),7.15(t,J=9.2Hz,1H),3.06(brs,1H),1.53(s,6H);

[0...

Embodiment 2

[0039]

[0040] Add 1 mol formula (I) compound, 2.15 mol sodium carbonate and 1.8 mol isopropyltriphenylphosphine bromide successively in the reactor at room temperature, and keep stirring under oxygen atmosphere, then add 7L DMSO and mass ratio thereto 1:0.7:0.5 of N,N-diisopropylethylamine (DIPEA), SmI 2 and a mixture additive of ferrocene (total mass is 4000g), the mixture is continuously stirred under an oxygen atmosphere at room temperature, and reacted for a total of 15h. After the reaction is completed, ethyl acetate is added for dilution, followed by washing with salt water and extraction with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified by column chromatography to obtain the compound of formula (II) with a yield of 96.9% and a purity of 98.6% (HPLC).

[0041] 1 H NMR (400MHz, CDCl 3 )δ=9.26(s,1H),8.73(d,J=4.8Hz,1H),8.30(d,J=8.0Hz,1H),7.45-7.42(m,1H),3.57(brs,1H), 1.6...

Embodiment 3

[0044]

[0045] Add 1 mol formula (I) compound, 2.1 mol sodium carbonate and 1.9 mol isopropyltriphenylphosphine bromide successively in the reactor at room temperature, and keep stirring under oxygen atmosphere, then add 9L DMSO and mass ratio thereto 1:0.7:0.5 of N,N-diisopropylethylamine (DIPEA), SmI 2 and a mixture additive of ferrocene (total mass is 5000g), the mixture is continuously stirred under an oxygen atmosphere at room temperature, and reacted for a total of 17h. After the reaction is completed, ethyl acetate is added for dilution, followed by washing with salt water and extraction with ethyl acetate. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo, and the residue was purified by column chromatography to obtain the compound of formula (II) with a yield of 96.3% and a purity of 98.4% (HPLC).

[0046] 1 H NMR (400MHz, CDCl 3 )δ=7.91(d,J=3.6Hz,1H),7.67(d,J=5.2Hz,1H),7.14(t,J=5.2Hz,1H),3.42(brs,1H),1.63(s, 6H); ...

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Abstract

The invention relates to a novel synthesis method for a three-stage alpha-hydroxyl carbonyl compound. According to the method, the carbonyl compound is taken as a raw material, sodium carbonate is taken as a catalyst, and proper types of additives and assistants are used, thus effectively building up a novel catalytic reaction system and further preparing the three-stage alpha-hydroxyl carbonyl compound at high yield. The reaction does not need an expensive noble metal catalyst or a complicated polymer catalyst, and shows advantages of high reaction yield, short time and the like. Therefore, the method has broad industrial application prospect and potential market value.

Description

technical field [0001] The invention relates to a method for synthesizing tertiary alcohol compounds, more specifically to a method for synthesizing tertiary α-hydroxycarbonyl compounds, and belongs to the field of organic chemical synthesis. Background technique [0002] The tertiary α-hydroxycarbonyl functional group is a special building block in organic chemistry, which exists in many biologically active compounds and synthetic drugs, such as paeonifloride B, erythrobimycin, emblic acid and polytetracycline, etc. Wait. In addition, this group can also be used as a high-efficiency photoinitiator for UV-curable coatings in the coatings industry. Therefore, the synthesis of tertiary α-hydroxycarbonyl compounds has received extensive attention. [0003] The preparation of tertiary α-hydroxycarbonyl compounds mainly involves the reaction of C-H hydroxylation. There are many types of C-H hydroxylation reactions in the prior art, such as: [0004] Charles E. Frank ("Hydroca...

Claims

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Application Information

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IPC IPC(8): C07C49/82C07C49/245C07C45/64C07D213/50C07D333/22B01J31/26
CPCC07C45/64C07D213/50C07D333/22C07C49/82C07C49/245
Inventor 李娜
Owner CHINA UNIV OF GEOSCIENCES (BEIJING)
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