Search research articles

ABOUT JoVE

Overview Leadership Blog JoVE Help Center

AUTHORS

Publishing Process Editorial Board Scope & Policies Peer Review FAQ Submit

LIBRARIANS

Testimonials Subscriptions Access Resources Library Advisory Board FAQ

RESEARCH

JoVE Journal Methods Collections JoVE Encyclopedia of Experiments Archive

EDUCATION

JoVE Core JoVE Business JoVE Science Education JoVE Lab Manual Faculty Resource Center Faculty Site

Terms & Conditions of Use

Related Concept Videos

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis

Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
In this method, in the presence of protic acids, alcohol dehydrates to produce alkenes and ethers under different conditions. For example, in the presence of sulphuric acid, dehydration of ethanol at 413 K yields ethoxyethane, whereas it yields ethene at 443 K.

Multiple Halogenation of Methyl Ketones: Haloform Reaction

Multiple Halogenation of Methyl Ketones: Haloform Reaction

A method involving the transformation of methyl ketones to carboxylic acids using excess base and halogen is called the haloform reaction. It begins with the deprotonation of α hydrogen to form an enolate ion which reacts with the electrophilic halogen to give an α-halo ketone. The step continues until all the α protons are substituted to form a trihalomethyl ketone. The resulting molecule is unstable, and in the presence of a hydroxide base, it readily undergoes nucleophilic...

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by

Same author

Adsorption-Biased, Halide-Tuned Perovskite Photocatalysts for Aerobic Oxidation of Primary Alcohols to Benzimidazoles.

Journal of the American Chemical Society·2026

Same author

A readily accessible CH anion transfer reagent for the preparation of a molybdenum methylidyne complex.

Chemical science·2026

Same author

Photocatalyzed Epimerization of Quaternary Stereocenters.

Journal of the American Chemical Society·2025

Same author

Solution-phase synthesis of alloyed Ba(Zr<sub>1-</sub>Ti<sub></sub>)S<sub>3</sub> perovskite and non-perovskite nanomaterials.

Nanoscale·2024

Same author

Synthesis and Characterization of Bipyridyl-(Imidazole)<sub>n</sub> Mn(II) Compounds and Their Evaluation as Potential Precatalysts for Water Oxidation.

Molecules (Basel, Switzerland)·2023

Same author

Solution-phase synthesis of group 3-5 transition metal chalcogenide inorganic nanomaterials.

Chemical communications (Cambridge, England)·2023

Search research articles

Related Experiment Video

Updated: Jul 10, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

(4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol.

Ryan B Gaynor¹, Baylee N McIntyre¹, Sidney E Creutz¹

¹Department of Chemistry, Mississippi State University, Mississippi State, MS 39762, USA.

|November 20, 2023

Summary

A novel adamantane-imidazole derivative was synthesized in five steps with a 28% overall yield. This compound shows potential as a precursor for biomimetic chelating ligands.

Keywords:

bioinspired imidazoles ligand precursors

More Related Videos

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Related Experiment Videos

Last Updated: Jul 10, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Published on: January 19, 2016

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

Area of Science:

Organic Chemistry
Medicinal Chemistry

Background:

Adamantane and imidazole moieties are prevalent in pharmacologically active compounds.
Biomimetic chelating ligands are crucial for various therapeutic and diagnostic applications.

Purpose of the Study:

To synthesize a novel (4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol compound.
To explore its potential as a precursor for biomimetic chelating ligands.

Main Methods:

A five-step synthetic route was employed, starting from 1-acetyladamantane.
Characterization was performed using nuclear magnetic resonance (NMR) spectroscopy, high-resolution mass spectrometry, and elemental analysis.

Main Results:

The target compound was successfully synthesized with moderate-to-excellent yields in each step.
An overall yield of 28% was achieved across the five-step process.
Comprehensive spectroscopic and analytical data confirmed the compound's structure and purity.

Conclusions:

The successful synthesis of (4-(Adamantan-1-yl)-1-(isopropyl)-1H-imidazol-2-yl)methanol provides a new chemical entity.
This compound and its derivatives represent promising precursors for developing novel biomimetic chelating ligands.