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A kind of preparation method of fluorolactone intermediate

A technology of methyl acrylate and compounds, which is applied in the field of organic chemistry and the preparation of fluorolactone intermediates, and can solve problems such as instability and affecting product quality standards

Active Publication Date: 2016-04-13
浙江瑞博制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The Wittig reagent is active in nature and unstable to water and air; and the reaction of the Wittig reagent with the corresponding aldehyde to generate olefins is accompanied by the generation of triphenylphosphine oxide, so column chromatography purification is required, but triphenyl Phosphine oxide is difficult to completely remove and easily remains in the product, thus affecting the quality standard of the product

Method used

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  • A kind of preparation method of fluorolactone intermediate
  • A kind of preparation method of fluorolactone intermediate
  • A kind of preparation method of fluorolactone intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Preparation of 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylene-3-hydroxyl-2-acrylate

[0031] Put (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (65g, 0.5mol), tri-n-butylamine (40g, 0.22 mol) and methyl acrylate (65g, 0.76mol), heat up to 30-40°C, keep warm for 16 hours, add 300ml of dichloromethane and 100ml of water into the reaction flask, stir, separate layers, and wash the organic layer with 2*100ml of water 2 times, and then washed once with 100ml 10% acetic acid, and finally washed once with 50ml saturated sodium bicarbonate solution, and the organic layer was concentrated under reduced pressure to remove dichloromethane and low boiling point substances to obtain 3-[(4R)-2,2 84 g of -methyl-dimethyl-1,3-dioxolan-4-yl]-2-methylene-3-hydroxy-2-acrylate, yield 68.3%, GC purity 93.5%.

example 2

[0032] Example 2: Preparation of 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylene-3-hydroxyl-2-acrylate

[0033] (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (65g, 0.5mol), DBU (30g, 0.2mol), Methyl acrylate (65 g, 0.76 mol) and 200 ml of dichloromethane were heated to reflux and kept for 8 hours. Cool, add 100ml of dichloromethane and 100ml of water to the reaction bottle, stir, separate layers, wash the organic layer 2*100ml of water twice, then wash with 100ml of 10% acetic acid once, and finally wash with 50ml of saturated sodium bicarbonate solution for 1 Second, the organic layer was concentrated under reduced pressure to remove dichloromethane and low boiling point substances to obtain 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylene 91.67 g of methyl-3-hydroxy-2-acrylate, yield 75.8%, GC purity 95.1%.

example 3

[0034] Example 3: Preparation of 3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methylene-3-hydroxyl-2-acrylate

[0035] Put (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (32g, 0.25mol) into a 500ml reaction flask, 8 grams of trimethylphosphine (8g , 0.1mol), 1,1'-bi-2-naphthol (5g, 0.017mol), methyl acrylate (30g, 0.35mol) and 300mlTHF, heated to 50-60°C and kept for 16 hours. Concentrate under reduced pressure to remove THF, add 250ml of dichloromethane to the residue, wash with 100ml of water, 100ml of 20% sodium carbonate solution, and 50ml of water, and concentrate the organic layer under reduced pressure to remove dichloromethane and low boiling point substances to obtain 3-[ (4R)-2,2-Dimethyl-1,3-dioxolan-4-yl]-2-methylene-3-hydroxy-2-methyl acrylate 49.2g, yield 80.1%, GC 93.6% purity.

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Abstract

The invention relates to the technical field of organic chemistry, and particularly a preparation method of a fluorine lactone intermediate. The method comprises the following step: preparing a compound disclosed as Formula I from a compound disclosed as Formula II in the presence of sodium borohydride and Lewis acid.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to the technical field of preparation of a fluorolactone intermediate. Background technique [0002] Lactone compounds widely exist in nature, they are not only the main functional groups of some natural products, such as alkaloids, macrocyclic antibiotics, lignan lactones, hormone lactones, plant growth regulators, spices, but also biologically active substances and metabolic intermediates; gradually, people noticed that the selective introduction of fluorine atoms in organic molecules can cause unexpected changes in their physiological activities, and the introduction of fluorine atoms or fluorine-containing groups into lactone compound molecules can make the compounds The shift of the electronic center of the electrons changes its biological activity, so this field appears to be increasingly active. Therefore, the synthesis of lactone compounds has always been a resear...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D317/30
CPCC07D317/30
Inventor 杜小华何大伟车大庆
Owner 浙江瑞博制药有限公司