Dabco → (Z)-isopropyl 3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylate

Participants

Reaction Steps

A 3-neck round-bottom flask was charged with a solution of 3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazole (2) (160 g, 1.0 eq.) in DMF (960 mL). The solution was treated DABCO (127.74 g, 2 eq.) and stirred for 30 min before being treated with (Z)-isopropyl 3-iodoacrylate (150.32 g, 1.1 eq.). After 1 hm the reaction mixture was poured into ice water slurry (5 L) and extracted with EtOAc (3×1 L). The combined organic layers were washed with brine (3×100 mL), dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure to afford 250 g of crude compound. Purification by column chromatography (silica gel, eluting with EtOAc/hexane) afforded 138 g (61% yield) of pure isopropyl ester (3).

Provenance & Evidence