TRANSFORMATION OF 5,6-DEHYDROKAWAIN THROUGH FLUORINATION REACTION USING SELECTFLUOR REAGENT

• Main Author: Vierlanda Hendy, Shalsa
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/65046
• Institution: Institut Teknologi Bandung

Compound 5,6-Dehydrokawain is a compound known to be contained in the Alpinia malaccensis plants. This compound is the main compound, so it is easy to obtain. In previous studies, the molecular diversification of the compound 5,6-Dehydrokawain has been carried out using the bases t-BuONa and MeONa. However, until now, the molecular diversification of the 5,6-dehydrokawain compound has never been carried out using a fluorination reaction. Selectfluor the commercially available and has very high stability and is relatively harmless, Selectfluor also does not show any signs of mutagenic or carcinogenic activity. Thus, Selectfluor can be used as the main fluorine donor in electrophilic fluorination. Based on this background, this study aims to transform and determine the structure of 5,6-dehydrokawain derivatives through fluorination reactions using Selectfluor. This transformation was carried out through several stages, namely the reaction stage and the purification stage using the radial chromatography (KR) technique. Chromatography results were analysed using thin layer chromatography (TLC). The pure compounds that have been obtained were determined for their structure by being characterized using 1D NMR (1H, 13C, 19F, zTOCSY-1D, ROESY-1D), 2D NMR (HSQC and HMBC), and MS. In this study, three new compounds have been successfully transformed from the fluorination reaction of 5,6-dehydrokawain, namely (3Z,5E)-1,1-Difluoro-4-hydroxy-6-phenylhexa-3,5-dien-2-one (1) with a yield of 12.2% in the reaction in acetonitrile, Methyl (E)-2,2-difluoro-3,3-dimethoxy-5-oxo-7-phenylhepta-6-enoate (2) with a yield of 47.8% in the reaction in methanol, and (E)-5-fluoro-4,6-dimethoxy-6-styryl-5,6-dihydro-2H-pyran-2-one (3) with a yield of 2.8% at reaction in acetonitrile methanol solvent.