Synthesis and scale-up of pinene pyrimidine type ligand

Blum, Caitlin (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Solea, Atena-Bianca (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland) ; Mamula Steiner, Olimpia (School of Engineering and Architecture (HEIA-FR), HES-SO // University of Applied Sciences Western Switzerland)

The aim of this Bachelor thesis was to synthesise a ligand of the pinene-pyrimidine type. Following the literature procedure, α-pinene (racemate) was chosen as starting material and four synthetic steps out of five have been optimised (see Fig. 2) In the first step the formation in situ of the reactant, NOCl, has been tested but the product, the nitrosochloro-derivate, was obtained with a lower yield (20%) compared to the procedure in which exogenous NOCl is bubbled through the reaction mixture (36%). Optimisation of the step 2 (formation of the pinocarvone oxime) was then performed in which various amines and bases were tested, and the highest yield obtained was 39%. The formation of the isoxazole (step 3) worked well and only the purification by distillation caused a decrease of yield to 48% because of the presence of iodine impurities and the small quantity of product to distil. Step 4 (formation of the enamine aldehyde by hydrogenation) was straightforward (yield 99%).


Article Type:
professionnel
Faculty:
Ingénierie et Architecture
School:
HEIA-FR
Institute:
ChemTech - Institut des technologies chimiques
Subject(s):
Chimie et science de la vie
Ingénierie
Date:
2019-03
Pagination:
2 p.
Published in:
À jour: Schweizerischer Verband diplomierter Chemiker FH = Association suisse des chimistes diplômés HES (SVC)
Numeration (vol. no.):
2019, Nr. 1/19, pp. 14-15
External resources:
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 Record created 2019-04-30, last modified 2019-04-30

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