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Faculté des Sciences
Faculté des Sciences
MASTER THESIS
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α-Hydroxylation of enolizable ketones under continuous flow conditions

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Toussaint, François ULiège
Promotor(s) : Monbaliu, Jean-Christophe ULiège
Date of defense : 1-Jul-2019 • Permalink : http://hdl.handle.net/2268.2/6932
Details
Title : α-Hydroxylation of enolizable ketones under continuous flow conditions
Author : Toussaint, François ULiège
Date of defense  : 1-Jul-2019
Advisor(s) : Monbaliu, Jean-Christophe ULiège
Committee's member(s) : Lemaire, Christian ULiège
Lecomte, Philippe ULiège
Damblon, Christian ULiège
Language : English
Number of pages : 57
Keywords : [fr] continuous-flow, hydroxylation, enolizable ketones
Discipline(s) : Physical, chemical, mathematical & earth Sciences > Chemistry
Research unit : Center for Integrated Technology and Organic Synthesis
Target public : Researchers
Professionals of domain
Institution(s) : Université de Liège, Liège, Belgique
Degree: Master en sciences chimiques, à finalité approfondie
Faculty: Master thesis of the Faculté des Sciences

Abstract

[fr] α-hydroxyketone derivatives are organic scaffolds widely encountered in natural or pharmaceutical active compounds. Many synthetic routes were reported in the literature but within the actual context of developing greener chemical processes, strategies involving transition-metal free synthesis using widely available molecular oxygen as the oxidizing source will be considered. Procedures for the hydroxylation of ketones with molecular oxygen have been already reported in batch but left with quite unresolved safety issues. This work aimed at developing a continuous-flow system allowing the safe hydroxylation of ketone-substrates using the intrinsic properties of flow chemistry.
Herein, we report a green and safe continuous flow procedure towards the synthesis of α-hydroxylated ketones. Conditions were first developed on a model substrate, namely, isobutyrophenone. The reaction conditions involved FDA class 3 and Chem21 green solvents, including ethanol and DMSO, as well as reactants presenting a low toxicity profile. Once all parameters were optimized, the conditions were applied to a small library of substrates to assess its efficiency. Enolizable ketones or esters were selected as potential substrates. Our procedure was then used for the synthesis of an important α-hydroxylated ketone intermediate for the preparation of active pharmaceutical ingredient ketamine. This synthesis worked efficiently under our conditions since total conversion and selectivity was achieved. The reaction conditions were next transposed to a larger mesofluidic pilot scale reactor, thus enabling the preparation of 1.3 kg per day with high conversions and selectivity.


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Author

  • Toussaint, François ULiège Université de Liège > Master en sc. chimiques, à fin.

Promotor(s)

Committee's member(s)

  • Lemaire, Christian ULiège Université de Liège - ULiège > CRC In vivo Imaging-Radiochemistry
    ORBi View his publications on ORBi
  • Lecomte, Philippe ULiège Université de Liège - ULiège > Département de chimie (sciences) > Centre d'études et de rech. sur les macromolécules (CERM)
    ORBi View his publications on ORBi
  • Damblon, Christian ULiège Université de Liège - ULiège > Département de chimie (sciences) > Chimie biologique structurale
    ORBi View his publications on ORBi
  • Total number of views 40
  • Total number of downloads 6










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