Method for preparing 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane

A technology of alkoxydiphenylethane and trimethoxy, which is applied in the field of synthesis of alkoxydiphenylethane derivatives, and achieves the effects of simple operation method, remarkable technological progress and easy control of synthesis conditions

Inactive Publication Date: 2014-01-29
SHANGHAI INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009]2. The reduction of methoxy group to hydroxyl group needs to be carried out under harsh conditions such as anhydrous and oxygen-free conditions, and more expensive reagents such as organolithium are required ,
[0010]3. Some steps require the use of toxic solvents such as benzene,
[0011] All in all, the reported synthetic routes have long steps and expensive reagents, resulting in high cost of raw materials

Method used

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  • Method for preparing 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane
  • Method for preparing 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1 compound 2 That is, the preparation of 3-benzyloxy-4-methoxybenzaldehyde

[0035] A dry 500ml oblique three-necked flask with a condenser, mechanically stirred, put in 19.85g (87.06mmol) of the compound 1 , dissolved in 100ml of acetonitrile, heated to 40°C in an oil bath, and added 9.33g (88.04mmol) of Na 2 CO 3 , continue to heat up to 60° C., add 8 ml of methyl bromide, continue to add 8 ml of methyl bromide after 3 hours, and react overnight.

[0036] After the reaction, the system was cooled to room temperature and quenched with 100ml of water, extracted with ethyl acetate, washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated and dried, and washed twice with petroleum ether to obtain 20 grams of a white solid. The yield is 95%.

[0037] 1 H NMR (CDCl 3 ) δ(ppm): 9.82 (s, 1H), 7.32-7.46 (m, 7H), 7.00(d, 1H), 5.20 (s, 2H), 3.97 (s, 3H).

Embodiment 2

[0038] Example 2 compound 2 That is, the preparation of 3-benzyloxy-4-ethoxybenzaldehyde

[0039] A dry 500ml oblique three-necked flask with a condenser, mechanically stirred, put in 19.85g (87.06mmol) of the compound 1 , dissolved in 100ml of isopropanol, heated in an oil bath to 40°C, and added 12.15g (88.04mmol) of K 2 CO 3 , continue to heat up to 60°C, add 10ml of bromoethane, continue to add 10ml of bromoethane after 3 hours, continue to react for 3 hours, after TLC detects that the reaction is complete, the system cools down to room temperature, quenches the reaction with 100ml of water, and extracts with ethyl acetate Finally, it was washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated and dried, and washed twice with petroleum ether to obtain 19.8 g of a white solid with a yield of 89%.

[0040] 1 H NMR (CDCl 3 ) δ(ppm): 9.81 (s, 1H), 6.98-7.47 (m, 8H), 5.20 (s, 2H), 4.18-4.22 (q, 2H), 1.49-1.52 (t, 3H).

Embodiment 3

[0041] Example 3 Compound 2 That is, the preparation of 3-benzyloxy-4-propoxybenzaldehyde

[0042] A dry 500ml oblique three-necked flask with a condenser, mechanically stirred, put in 19.85g (87.06mmol) of the compound 1 , dissolved in 100ml of DMF, heated to 60°C in an oil bath, added 4.93g (88.04mmol) of KOH, continued to heat up to 80°C, added 12ml of bromopropane, continued to add 12ml of bromopropane after 3 hours, and reacted overnight.

[0043] After the reaction, the system was cooled to room temperature and quenched with 100ml of water, extracted with ethyl acetate, washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated and dried, washed twice with petroleum ether to obtain 18.8 grams of a white solid. The rate is 80%.

[0044] 1 H NMR (CDCl 3 ) δ(ppm): 9.85(s, 1H), 7.20-7.48 (m, 8H), 5.20(s, 2H), 3.90 (t, 2H), 1.79 (m, 2H), 0.96 (t, 3H).

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Abstract

The invention provides a method for preparing 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane. The method comprises the steps of firstly enabling 3-benzyloxy-4-hydroxybenzaldehyde and alkyl bromide to be subjected to alkoxylation reaction, so as to obtain a compound (2) shown in a drawing, then, enabling 3,4,5-trimethoxybenzyl triphenyl phosphine bromate and the compound (2) to be subjected to Wittig reaction, so as to prepare a compound (4) shown in a drawing, and finally, carrying out reduction on the compound (4) by palladium on carbon / hydrogen gas at normal pressure, thereby obtaining the target compound 3,4,5-trimethoxy-3'-hydroxy-4'-alkoxy diphenylethane. According to the method, the synthesis method is simple and reasonable, the operation is simple and convenient, the yield is high, the cost is low, the use of high-toxicity solvents, such as benzene, is avoided, the method is environmental-friendly, and the industrial production is facilitated.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and relates to a method for synthesizing alkoxydiphenylethane derivatives, specifically a 3, 4, 5-trimethoxy-3'-hydroxyl-4'-alkoxy The preparation method of diphenylethane. Background technique [0002] In 1971, Folkman first proposed the theory of angiogenesis, and believed that the vascular system of tumors plays an important role in the process of tumor growth, development and metastasis. If tumor angiogenesis is inhibited, some tumor cells will die due to ischemia and hypoxia, thereby delaying the development of tumor growth. Tumor growth and inhibition of tumor metastasis (Folkman, J., et al. J. Med. 1971, 285, 1182-1186). It has been proved that tumor growth must depend on angiogenesis, which provides a new target for tumor therapy. At present, scientific research institutions in many regions of the world have launched the research and development of new drugs for tumor vascular targeted...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C43/23C07C41/26
CPCC07C41/26C07C41/30C07C45/64
Inventor 庞婉赵磊周九九吴范宏
Owner SHANGHAI INST OF TECH
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