作为一个有效的TMS来源的MSTFA为TMSOTf-催化合成循环乙
Suttipol Radomkit1, Jada A H White1, Eugene Chong1
1Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road, P.O. Box. 368, Ridgefield, Connecticut 06877-0368, United States.
The Journal of organic chemistry
|April 9, 2024
概括
这项研究引入了2,2,2-三-N-甲基-N-(三甲基) 乙胺 (MSTFA) 作为合成循环乙的高效三甲基源. 在温和条件下,MSTFA提供了一种方便且高收益的方法,避免了常见的副作用抑制.
科学领域:
- 有机合成 有机合成
- 绿色化学 绿色化学
- 催化剂是一种催化剂.
背景情况:
- 循环乙是有机化学中重要的结构动图.
- 循环乙合成的传统方法通常需要恶劣的条件或过多的试剂.
- 化剂通常用于有机合成,但有些可以抑制催化过程.
研究的目的:
- 确定一个高效的三甲基 (TMS) 源,方便制备循环乙.
- 开发一种温和高效的方法来合成广泛的循环乙.
- 为了克服与现有的化试剂在乙化反应中的局限性.
主要方法:
- 使用商业上可用的2,2,2-trifluoro-N-methyl-N-(trimethylsilyl) acetamide (MSTFA) 作为TMS的来源.
- 员工用催化三甲基三甲硫酸盐 (TMSOTf) 修改了诺约里的条件.
- 研究了反应与各种二醇的兼容性,并将MSTFA与其他化剂 (BSA,BSTFA) 进行了比较.
主要成果:
- MSTFA被证明是一个高效的TMS来源,使得循环乙的方便制备.
- 在温和的条件下,反应顺利进行,产生了各种各样的循环乙,产量很好.
- 使用MSTFA避免了由副产品引起的催化乙化抑制,与BSA和BSTFA不同.
结论:
- MSTFA是有效和温和合成循环乙的有价值的试剂.
- 开发的方法提供了优势,因为不需要大量的二醇或预合成的化二醇.
- 由于它避免了催化抑制,MSTFA代表了与其他化试剂的改进.
相关概念视频
01:24Acetals and Thioacetals as Protecting Groups for Aldehydes and Ketones
4.1K
Acetals are formed by reacting two equivalents of alcohol with carbonyl compounds like aldehydes or ketones. Acetals are unaffected by bases, nucleophiles, oxidizing agents, and reducing agents. They serve as protecting groups for aldehydes and ketones. Acetals can be easily formed and also easily removed via mild acid hydrolysis.
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
In the presence of multiple functional groups, when selective reduction of one group over the other is desired, groups like aldehydes and ketones that form acetals...
4.1K
01:13Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism
7.8K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
7.8K
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
3.3K
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
3.3K
01:20Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Overview
18.0K
The Fischer esterification reaction was developed by the German chemist Emil Fischer in 1895. It is a condensation reaction between carboxylic acids and alcohols in an acidic medium to give esters and water.
18.0K
02:27Preparation of Alkynes: Alkylation Reaction
10.1K
Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
10.1K
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
3.4K
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
3.4K