Acetic Anhydride → HCID 86745842, compound

Participants

Reaction Steps

Activated zinc powder (496 mg), powdered molecular sieve 4A (1.25 g) (ex. BDH) and cuprous chloride (84 mg) were suspended in anhydrous tetrahydrofuran (10 ml). (2E)-10-(2-Quinolinyloxy)dec-2-enal (1 g) was added followed by acetic anhydride (320 μl). The mixture was warmed to 50° under nitrogen and methyl fluorodichloroacetate (328 μl) was added. The mixture was warmed at 50-5° for 4 hours, additional zinc (0.2 g) was added and warming continued for 30 minutes. Upon cooling the reaction mixture was diluted with diethyl ether, filtered through celite and filtrate worked-up in standard fashion. Purification by column chromatography (silica; 4;1, hexane: ether) gave (2Z,4E) methyl 2-fluoro-12-(2-quinolinyloxy)dodeca-2,4-dienoate (0.26 g).

Provenance & Evidence