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Synthesis method of ethyl 2,2-difluorohexanoate

A technology of ethyl difluorohexanoate and dosage, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve the problems of inconvenient synthesis and high price of ethyl iodide difluoroacetate, and achieve production Low cost, high economic value, and convenient synthesis

Inactive Publication Date: 2011-11-16
SHANGHAI FLUOROTECH SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0009] In [J.Org.Chem., 1992, 57 (19), 5144-5149] reported that Yang Zhenyu et al. reacted ethyl iododifluoroacetate with butene to synthesize 2,2-difluoroethyl hexanoate, and the reaction conditions Mild, easy to operate, but the price of ethyl iododifluoroacetate is high and the synthesis is inconvenient

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  • Synthesis method of ethyl 2,2-difluorohexanoate
  • Synthesis method of ethyl 2,2-difluorohexanoate

Examples

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Embodiment 1

[0024] Add Zn (0.2mol, 11.2g) and NiCl to a three-necked flask (250mL) 2 .6H 2 O (0.01 mol, 0.167 g) and then THF (80 mL) was added. Add BrCF dropwise at 35℃ 2 COOEt (0.1mol, 20.3g), after reaction for 0.5h, add dropwise a THF solution of butene (0.4mol, 22.4g) at 35°C for 0.5-1.0h. After reacting at 15°C for 5.0h, 19 F NMR monitors the reaction. The reaction solution was poured into a saturated ammonium chloride solution, extracted with ether, washed with water 4 times, dried with sodium sulfate, and evaporated at atmospheric pressure to remove the ether and recover the ether. Pump vacuum distillation to obtain 2,2-difluorohexanoic acid ethyl ester (0.0856mol, 15.4g) with a yield of 85.6%.

Embodiment 2

[0026] Add Zn (0.2mol, 11.2g) and NiCl to a three-necked flask (250mL) 2 .6H 2 O (0.01 mol, 0.167 g) and then THF (100 mL) was added. Add BrCF dropwise at 40℃ 2 COOEt (0.1mol, 20.3g), after reacting for 1.0h, a THF solution of butene (0.4mol, 22.4g) was added dropwise at 40°C for 1.0h. After reacting at 20°C for 5.0h, 19 F NMR monitors the reaction. The reaction solution was poured into a saturated ammonium chloride solution, extracted with ether, washed with water 6 times, dried with sodium sulfate, and evaporated at atmospheric pressure to remove the ether and recover the ether. Pump vacuum distillation to obtain 2,2-difluorohexanoic acid ethyl ester (0.0856mol, 15.8g), the yield was 86%.

Embodiment 3

[0028] Add Zn (0.4mol, 22.4g) and NiCl to a three-necked flask (250mL) 2 .6H 2 O (0.02mol, 0.334g) and then THF (120mL) was added. Add BrCF dropwise at 37℃ 2 COOEt (0.2mol, 40.6g), after reacting for 0.7h, a THF solution of butene (0.4mol, 22.4g) was added dropwise at 38°C for 0.8h. After reacting at 18°C ​​for 5.0h, 19 F NMR monitors the reaction. The reaction solution was poured into a saturated ammonium chloride solution, extracted with ether, washed with water 5 times, dried with sodium sulfate, and evaporated to remove the ether and recover the ether under normal pressure. Water pump vacuum distillation, 2,2-difluorohexanoic acid ethyl ester (0.0816mol, 14.7g) was obtained, and the yield was 81.6%.

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Abstract

The invention discloses a synthesis method of ethyl 2,2-difluorohexanoate. The method is characterized by comprising the following steps of: blending of a catalyst, occurrence of a main reaction, and extraction and rectification of a product. In the invention, by screening the common metal iron, copper and zinc, zinc is finally employed; through the optimization of the solvents of DMSO (dimethyl sulfoxide), CH3CN (acetonitrile), DMF (dimethyl formamide) and THF (tetrahydrofuran), THF is adopted as the solvent; and by means of screening various catalysts like palladium and nickel, etc., NiC12. 6H2O is finally taken as the catalyst. Synthesis of ethyl 2,2-difluorohexanoate with the method of the invention is not only low in cost but also convenient for synthesis. With a stable yield of 80-85%, the method provided in the invention has high economic value, thus suitable for large scale industrial production.

Description

Technical field [0001] The present invention relates to a method for synthesizing ethyl 2,2-difluorohexanoate. Background technique [0002] Lubiprostone (Lubiprostone) has emerged as a therapeutic agent with a new mechanism of action, and it is quite promising as a medicine for treating constipation. Lubiprostone is a bicyclic fatty acid compound, which can effectively activate Cl in the intestine - Channel, increase the secretion of intestinal water, and increase the Cl of intestinal fluid - Concentration without affecting K + And Na + concentration. Lubiprostone has been approved by the US FDA and is the only drug used to treat irritable bowel syndrome and intestinal obstruction. [0003] In the existing literature records, Lubiprostone has two synthetic routes, see [Drugs of theFuture, 2004, 29(4), 336-341]: [0004] 1) From the commercially available Corey's lactone (I), remove TMS to obtain Carbinol, which is then oxidized to form an aldehyde, which is condensed with 2',2'-di...

Claims

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Application Information

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IPC IPC(8): C07C69/63C07C67/343B01J27/138
Inventor 张巍江静
Owner SHANGHAI FLUOROTECH SCI
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