20.500.12556/RUL-139479 Optimizacija Sonogashirove reakcije med 4-bromoacetofenonom in 4-etinil-N,N-dimetilanilinom Optimisation of the Sonogashira reaction between 4-bromoacetophenone and 4-ethynyl-N,N-dimethylaniline 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. 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. Sonogashirova reakcija 4-bromoacetofenon 4-etinil-N N-dimetilanilin Sonogashira reaction 4-bromoacetophenone ethynyl-N N-dymethylamine true false false Slovenski jezik Angleški jezik Diplomsko delo/naloga 2022-09-02 15:40:00 2022-09-02 15:40:04 2022-10-13 13:15:35 0000-00-00 00:00:00 2022 0 0 0000-00-00 NiDoloceno NiDoloceno NiDoloceno 0000-00-00 0000-00-00 0000-00-00 22002 125498627 Turk_Matevz_-_Optimizacija_Sonogashirove_reakcije_med_4-bromoacetofenonom_in_4-etinil-N,N-dimeti.pdf Turk_Matevz_-_Optimizacija_Sonogashirove_reakcije_med_4-bromoacetofenonom_in_4-etinil-N,N-dimeti.pdf 1 790E766898C363363B782AEC2E3AE743 954dd31dca028f08f05be3cf83303d9b331615d69bb152e2f4db855beeab932d b556a67a-2ac4-11ed-92af-00155dcfd717 https://repozitorij.uni-lj.si/Dokument.php?lang=slv&id=160050 Fakulteta za kemijo in kemijsko tehnologijo 0 0 0