REACTION STUDY OF 5,6-DEHYDROKAWAIN WITH SELECTFLUORTM

• Main Author: Paramita, Suci
• Format: Theses
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/70331
• Institution: Institut Teknologi Bandung

The compound 5,6-dehydrokawain (1) is a secondary metabolite is a major component in the leaves and rhizomes of the Alpinia zerumbet plant. The compound structure of (1) containing the 2-pyrone have been used as key intermediates in the synthesis of biogycally active compounds due to the presence of an electron-rich conjugated diene and ester group. In this study, the transformation was carried out using selectfluorTM (2) as an electrophilic fluorination reagent. SelectfluorTM (2) is a stable electrophilic fluorination reagent, non-hygroscopic and low toxicity. Based on this background, this study aims to transform and determine the structure of 5,6-dehydrokawain derivative (1) through fluorination reaction using selectfluorTM (2) in acetonitrile : isopropyl alcohol solvent and acetonitrile : ethylene glycol solvent. The transformation was carried out through reaction stage, fractionation stage, and purification stage using liquid vacuum chromatography (KCV) and radial chromatography (KR) techniques. Analysis of chromatography results was carried out using thin layer chromatography (KLT). Pure compounds that have been successfully obtained were then determined by characterizing their structure using 1D NMR (1H, 13C, 19F), 2D NMR (HSQC and HMBC), and MS. In this research, five compounds from the fluorination reaction of 5,6-dehydrokawain (1) have been successfully transformed, (E)-5-fluoro-6-isopropoxy-4-methoxy-6-styril-5,6-dihydro-2H-piran-2-on (3) with a yield of 4,5% in acetonitrile isopropyl alcohol, (E)-3-fluoro-5,6-dehydrokawain (4) with a yield of 2.2% in acetonitrile isopropyl alcohol, (E)-5-fluoro-6-(2-hydroxyethoxy)-4-methoxy-6-styryl-5,6-dihydro-2H-pyran-2-on (5a) with a yield of 8.1% in acetonitrile ethylene glycol, (E)-5-fluoro-6-(2-hydroxyethoxy)-4-methoxy-6-styril-5,6-dihydro-2H-pyran-2-on (5b) with a yield of 12,1% in acetonitrile ethylene glycol, 2-hydroxyethyl (E)-2,2-difluoro-2-(2-(2-oxo-4-phenylbut-3-en-1-yl)1,3-dioxolan-2-yl)acetate (6) with a yield of 37.8% in acetonitrile ethylene glycol.