The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of beta-hydroxy-beta-trifluoromethyl ketones from enamines and imines.

doi:10.1021/JO026697J

Paper

The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of beta-hydroxy-beta-trifluoromethyl ketones from enamines and imines.

Published Mar 12, 2003 · K. Funabiki, Kei Matsunaga, M. Nojiri

The Journal of organic chemistry

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33

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1

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Abstract

The reaction of trifluoroacetaldehyde ethyl hemiacetal or hydrate with an equimolar amount of enamines, derived from various methyl ketones, smoothly proceeded to give the corresponding beta-hydroxy-beta-trifluoromethyl ketones in high yields. An equimolar amount of imines derived from various methyl ketones with aliphatic, aromatic, and heteroaromatic substituents also readily reacted with trifluoroacetaldehyde ethyl hemiacetal or hydrate to afford the corresponding beta-hydroxy-beta-trifluoromethyl ketones in good to excellent yields. Difluoroacetaldehyde ethyl hemiacetal as well as pentafluoropropionaldehyde also participated in the reaction, affording good yields of the corresponding beta-hydroxy-beta-difluoromethyl or beta-pentafluoropropyl ketones.

Study Snapshot

Trifluoroacetaldehyde ethyl hemiacetal or hydrate is a simple and practical regioselective synthesis method for beta-hydroxy-beta-trifluoromethyl ketones from enamines and imines.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

The use of trifluoroacetaldehyde ethyl hemiacetal or hydrate in a simple and practical regioselective synthesis of beta-hydroxy-beta-trifluoromethyl ketones from enamines and imines.

References

Citations

Direct Synthesis of 2-Hydroxytrifluoroethylacetophenones via Organophotoredox-Mediated Net-Neutral Radical/Polar Crossover

This study presents a simple, cost-effective method for synthesis of 2-hydroxytrifluoroethylacetophenones from styrene derivatives via photoredox catalysis, using an organic photocatalyst and DMSO as oxidant.

Switchable Multicomponent Cyclization Reactions to Access Fluoroalkylated Dihydropyrimidines and Pyrimidines under Solvent‐Free Conditions

Switchable solvent-free multicomponent reactions enable the construction of valuable fluorinated heterocycles, conforming to the green synthesis concept.

Detection of organic hydrates in reversed phase high performance liquid chromatography using recurrent approximation of their retention times

Organic hydrates can be detected in reversed-phase HPLC by recurrent approximation of retention parameters, with reversible formation occurring in concentration ranges C min to C max.

Formation and Chromatographic Detection of Organic Compound Hydrates

Organic compound hydrates can cause anomalous dependences on retention parameters in reversed-phase high-performance liquid chromatography, making their characterization difficult due to their instability.

Lewis Acid-Catalyzed Rearrangement of Fluoroalkylated Propargylic Alcohols: An Alternative Approach to β-Fluoroalkyl-α,β-enones

The developed Lewis acid-catalyzed Meyer-Schuster rearrangement offers moderate to high yields and high stereoselectivity for the synthesis of -fluoroalkyl-,-enones.