Economic, One-Pot Synthesis of Diethyl Furoxan Dicarboxylate

IF 3.1 3区化学 Q2 CHEMISTRY, APPLIED

Organic Process Research & Development Pub Date : 2024-09-25 DOI:10.1021/acs.oprd.4c00191

Michael Thoenen, Nicholas F. Scherschel, Davin G. Piercey

引用次数: 0

Abstract

Diethyl furoxan dicarboxylate (DFD) is a starting material for fields as diverse as drug discovery, energetics, and any application where a furoxan or furazan may be desired. As with many disubstituted furoxans, they are synthesized via the dimerization of the appropriate nitrile oxide. Past procedures to form DFD involve low-yield destructive nitrations, multiple steps, halogenated solvents, or heavy or precious metals. Although these methods are functional enough for lab-scale preparations of DFD, they do not hold up well for economical scale-up. Our reported procedure improves the synthesis of DFD such that it is available from economical and commercially available starting materials in a single-step, one-pot, high-yield (98.5%) synthesis of material with a trivial workup in high purity (98.2% by ¹H quantitative NMR against a 2,4,6-trimethoxy-1,3,5-triazene standard). This improved procedure requires no organic solvents or heavy metals and is the most scalable preparation for this material to date.

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经济、一步法合成呋喃香烷二甲酸二乙酯

呋喃二甲酸二乙酯（DFD）是一种起始原料，可用于药物研发、能源以及任何需要呋喃或呋喃赞的应用领域。与许多二取代呋喃类化合物一样，它们也是通过适当的氧化腈二聚合成的。过去形成 DFD 的程序涉及低产率的破坏性硝化反应、多个步骤、卤化溶剂或重金属或贵金属。虽然这些方法对于实验室规模的 DFD 制备来说足够实用，但对于经济规模的扩大却不太适用。我们报告的程序改进了 DFD 的合成方法，使其可以用经济实惠且市场上可买到的起始材料，通过单步、一锅、高产率（98.5%）合成出高纯度（根据 2,4,6-三甲氧基-1,3,5-三氮烯标准的 1H 定量 NMR 值为 98.2%）的材料。这种改进的程序不需要有机溶剂或重金属，是迄今为止这种材料最易扩展的制备方法。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Process Research & Development 化学-应用化学

CiteScore

6.90

自引率

14.70%

发文量

251

审稿时长

2 months

期刊介绍： The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.