Sodium Iodide → HCID 20058695, compound

Participants

Reaction Steps

Reacting 5-(2,4,5-trifluorophenyl)-4-pentyn-1-ol (Compound 43) with methanesulfonyl chloride and sodium iodide gives 5-(2,4,5-trifluorophenyl)-1-iodo-4-pentyne. Treatment of this iodide with zinc and copper cyanide, as in Example 2, gives the corresponding mixed cuprate. Addition of this cuprate to 4-[(3-oxo-4,4,4-trifluoro)-1-butynyl]-2-trimethylsilylfuran (Compound 37) and hydrogenating the adduct gives 4-[1-(2-oxo-3,3,3-trifluoro)propyl-6-(2,4,5-trifluorophenyl)]hexyl-2-trimethylsilylfuran (Compound 44). Oxidizing this furan (Compound 44) with singlet oxygen gives 4-[1-(2-oxo-3,3,3-trifluoro)propyl-6-(2,4,5-trifluorophenyl)]hexyl-5-hydroxy-2(5H)-furanone (Compound 14).

Provenance & Evidence