Methyl coumalate(Molecule 9) was placed under a 450-W Hanovia lamp in a Pyrex filter flask with CH2Cl2 (Dichloromethane is an organic solvent that can dissolve many organic compounds) at 158oC for 96 hours. The Hanovia lamp and the the Pyrex filter flask are needed for the photochemical reaction to form the photopyrone (Molecule 10). H2 in Pt/C (hydrogen in a platinum catalyst are used for the syn addition of H/H across multiple bonds to the corresponding alkane; it will add to the double bond in the bottom butene ring in Molecule 10, as well as protonate the O in the top ring in Molecule 10) was added and allowed to react for 4 hours (forming Molecule 11). Separately but at the same time, 8-aminoquinoline (1.2 equiv, 173.004 g) (the nucleophile that will attack the electrophilic C of the carbonyl) and EDC (1.2 equiv, 186.288 g) (used to activate phosphate groups and make them more reactive) were combined and allowed to react at 0oC to 23oC for 3 hours.  The 8-aminoquinoline solution was added to the main mixture immediately after the 4 hours of hydrogenation. This led to an expected yield of ~54% of (2-iodovinyl)benzene (Molecule 12).

 

 

Experimental