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Synthetic method of diethyl naphthylmethyl-tetrahydrofurfurylmalonate

A technology of naphthylmethyl tetrahydrofurfuryl malonate diester and synthesis method, applied in directions such as organic chemistry, can solve problems such as difficulty in solvent recovery, increased production cost, troublesome processing, etc., and achieves less environmental pollution and high recovery rate , the effect of easy operation

Active Publication Date: 2011-06-29
浙江清和新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

DMF and alcohol are miscible with water, and another solvent such as toluene must be added to extract the product in the post-treatment, resulting in difficulties in solvent recovery, and often due to emulsification, resulting in layering difficulties, resulting in troublesome post-reaction treatment and increased production costs.

Method used

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Experimental program
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Effect test

Embodiment 1

[0027] The molar ratio of the feed materials is dimethyl tetrahydrofurfurylmalonate: sodium methoxide: 1-chloromethylnaphthalene = 1.0:1.0:0.9, and the temperature for dropping 1-chloromethylnaphthalene is 80°C.

[0028] Dimethyl tetrahydrofurfurylmalonate (40g, 0.185mol) and 2-methyltetrahydrofuran (200g, 233ml) were added into the reaction flask, and sodium methoxide (10g, 0.185mol) was added in batches at 20-45°C. ), heated and refluxed for 0.5 hours, then slowly added dropwise 1-chloromethylnaphthalene (29.4g, 0.167mol) at 80°C, refluxed for 1 hour, cooled to 20-45°C, added purified water and stirred for 10 minutes, static After settling, the organic layer was separated, and the aqueous layer was extracted with 50 mL of 2-methyltetrahydrofuran × 2. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and 278.9 g of 2-methyltetrahydrofuran was recovered by rectification under normal pressure. The yield was 97.5%, and ...

Embodiment 2

[0030] The molar ratio of the feed materials is dimethyl tetrahydrofurfurylmalonate: sodium methoxide: 1-chloromethylnaphthalene = 1.0: 1.3: 1.0, and the temperature for dropping 1-chloromethylnaphthalene is 80°C.

[0031] Add dimethyl tetrahydrofurfurylmalonate (40g, 0.185mol) and 2-methyltetrahydrofuran (300g, 350ml) into the reaction flask, and add sodium methoxide (13g, 0.241mol) in batches at 20-45°C ), heated and refluxed for 0.5 hours, then slowly added dropwise 1-chloromethylnaphthalene (32.7g, 0.185mol) at 80°C, refluxed for 1 hour, cooled to 20-45°C, added purified water and stirred for 10 minutes, static After settling, the organic layer was separated, and the aqueous layer was extracted with 50 mL of 2-methyltetrahydrofuran × 2. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and 375.5 g of 2-methyltetrahydrofuran was recovered by rectification under normal pressure. The yield was 97.3%, and 56.1 g of di...

Embodiment 3

[0033] The molar ratio of the feed materials is dimethyl tetrahydrofurfurylmalonate: sodium methoxide: 1-chloromethylnaphthalene = 1.0: 1.2: 1.0, and the temperature for dropping 1-chloromethylnaphthalene is 80°C.

[0034] Add dimethyl tetrahydrofurfurylmalonate (40g, 0.185mol) and 2-methyltetrahydrofuran (200g, 233ml) into the reaction flask, and add sodium methoxide (12g, 0.222mol) in batches at 20-45°C ), heated and refluxed for 0.5 hours, then slowly added dropwise 1-chloromethylnaphthalene (32.7g, 0.185mol) at 80°C, refluxed for 1 hour, cooled to 20-45°C, added purified water and stirred for 10 minutes, static After settling, the organic layer was separated, and the aqueous layer was extracted with 2-methyltetrahydrofuran (50mL×2). The yield was 97.9%, and 56.7 g of dimethyl naphthylmethyltetrahydrofurfurylmalonate was obtained, with a yield of 86.1% and a gas phase purity of 99.0%.

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Abstract

The invention discloses a method for synthesizing menaphthyl tetrahydrofuryl ethyl malonate as shown in a formula (I). The synthesis method is as follows: sodium alkoxide is added into a 2-methyl tetrahydrofuran solution of the menaphthyl tetrahydrofuryl ethyl malonate as shown in a formula (II) in batch at a temperature of between 20 and 45 DEG C; after addition, the mixture is heated and refluxed for 0.5 to 2 hours, and 1-methylnaphthalene halide as shown in a formula (III) is slowly dripped into the mixture at a temperature of between 80 and 100 DEG C; the mixture is subjected to reflux reaction for 0.5 to 2 hours; and the menaphthyl tetrahydrofuryl ethyl malonate is obtained after after-treatment of a reaction liquid. Compared with the prior art, the method has the advantages that themenaphthyl tetrahydrofuryl ethyl malonate adopts a green solvent, namely 2-methyl tetrahydrofuran as a reaction solvent and is also directly taken as an extracting solvent; and the method has high yield of reaction products and high recovery rate of the solvent, is environment-friendly, and has good industrial application prospect.

Description

(1) Technical field [0001] The invention relates to a method for synthesizing naphthalenemethyltetrahydrofurfurylmalonate diester. (2) Background technology [0002] Dialkyl naphthylmethyltetrahydrofurfurylmalonate is an important precursor for the synthesis of naftidylfuramide oxalate, which is a potent anti-stroke and cerebral embolism and other cardiovascular and cerebrovascular diseases. Vasodilator drugs with unique curative effect have the characteristics of unique mechanism of action, safe and effective clinical medication, and few side effects, and are receiving more and more attention. [0003] The document synthesis method of naphthylmethyltetrahydrofurfurylmalonate dialkyl ester is mainly: tetrahydrofurfurylmalonate dialkyl ester forms sodium salt in NaH / DMF or sodium alkoxide / alcohol system, and then with 1 Synthesis of dialkyl naphthylmethyltetrahydrofurfurylmalonate by reaction of halomethylnaphthalene. Because sodium hydride is flammable and explosive, it is...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/16
Inventor 王平应素华符建琼王凌云林介邦张彬斐周美丽
Owner 浙江清和新材料科技有限公司
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