Optimizacija Sonogashirove reakcije med 4-bromoacetofenonom in 4-etinil-N,N-dimetilanilinom

Turk, Matevž (avtor), Košmrlj, Janez (mentor)

V sklopu diplomskega dela smo optimizirali reakcijske pogoje Sonogashirove reakcije med 4-bromoacetofenonom in 4-etinil-N,N-dimetilanilinom ter postopek izolacije nastalega produkta. Našli smo kombinacijo reakcijskih pogojev in mobilne faze za čiščenje produkta s preparativno kolonsko kromatografijo, s katero smo uspešno presegli zadan cilj 80% izkoristka. Optimiziran postopek smo preizkusili še na večji skali. 1-[4-[2-[4-(Dimetilamino)fenil]etinil]fenil]etanon, sintetiziran tekom optimizacije, smo dodatno očistili s preparativno kolonsko kromatografijo in okarakterizirali z 1H NMR, 13C NMR, IR in masno spektroskopijo, mu izmerili tališče ter določili njegovo čistost s HPLC.

• Jezik: Slovenski jezik
• Ključne besede: Sonogashirova reakcija, 4-bromoacetofenon, 4-etinil-N, N-dimetilanilin
• Vrsta gradiva: Diplomsko delo/naloga
• Tipologija: 2.11 - Diplomsko delo
• Organizacija: FKKT - Fakulteta za kemijo in kemijsko tehnologijo
• Leto izida: 2022
• PID: 20.500.12556/RUL-139479
• COBISS.SI-ID: 125498627
• Datum objave v RUL: 02.09.2022

Sekundarni jezik

• Jezik: Angleški jezik
• Naslov: Optimisation of the Sonogashira reaction between 4-bromoacetophenone and 4-ethynyl-N,N-dimethylaniline

Izvleček

As a part of my Bachelor's thesis we have optimised reaction conditions of the Sonogashira reaction between 4-bromoacetophenone and 4-ethynyl-N,N-dimethylaniline, and the isolation process of the formed product. We have discovered a combination of reaction conditions and a mobile phase, used in purification of the formed product by the means of preparative column cromatography, with which we have successfuly surpassed our goal of an 80% yield. We have further tested the optimised procedure on a larger scale. 1-[4-[2-[4-(Dimethylamino)phenyl]etinyl]phenyl]ethanone, synthesized during the optimization process, has been further purified using preparative column cromatography, and characterized by 1H NMR, 13C NMR, IR and mass spectroscopy, measuring of its melting point and determining its purity by HPLC.

• Ključne besede: Sonogashira reaction, 4-bromoacetophenone, ethynyl-N, N-dymethylamine