Synthesis of a butterfly shaped furan derivative
Today i wanted to share a synthesis i performed this week end that i found to be pretty interesting
The info and procedures come from the following paper :
https://pubs.acs.org/doi/10.1021/jo500085a
The 2,3 dihydronaphtalene was purchased online since it was easily accesible for me
In case of i prefered to dry all my reagent but am not sure it is required
Firstly a reflux apparatus was setup with a argon entry in order to inert the whole thing, following this 60ml of dried O xylene was added and argon
was bubbled trough it for a few minutes. Once the solvent was degased 1,6g of 2,3 dihydronaphtalene was added followed by 3.2ml of dry methane
sulfonic acid. The apparatus was then closed and heating to 130°C was started. During the 24h reflux the temp spiked to 150°c a few time cause of
the bad precision of my heating mantle. Some dark oil formed in suspension and the mix slowly took a tint reminding me of dilute fluoresceine in
sunlight
Following overnight reflux the mix was quenched with 50ml of saturated sodium carbonate solution and was then transfered into a separatory funnel
At this point i started to use dichloromethane rather than chloroform to extract it, however i noticed chloroform works way better in term of phase
separation and dissolution of suspended solid. I let the mix stand overnight to separate and extracted the aqueous phase with a dozen more ml of
solvent.
Once this was done the organic phase was dried and filtered on coton to be then evaporated on my rotavap. It was pretty hard to remove the o-xylene
left but i managed to drive it of after some time.
At this point the TLC showed a brightly fluorescent blue product with a high rf and no starting material left
The brown oil was dissolved in dichloromethane and silica 60 chromatography gel was added, the mix was then evaporated under vacuum to give the solid
deposit required for purification.
I then setup a vacuum flash chromatography using chloroform as a solvent and collected 27 tubes
After i performed a few tlc to determine the main product fractions and found out they were the 5 first tubes
Following evaporation i obtained around 650mg of a brown/orange powder (around 45% of yeild if it was 100% pure) with a melting point of around 219c
(close to the litterature value). Tlc of showed a single spot with a long trail left behind it probably because it was too concentrated. I would
probably need to do a NMR or LCMS but i will proceed toward the next step adding the same patern and make it symetrical in a few weeks and update on
how it went.
I noticed as well that the color of the glow seem to vary from blue to green/yellow depending of the concentration / if its in solution or not, am not
sure if this is the product itself or slight impurities causing that unfortunately
Anyway enjoy a few pics of synthesis and the beautiful glow of the final product <3
        
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