4,4,4-Trifluoro-but-2-ynoic acid benzyl ester → (E)-4,4,4-Trifluoro-3-[4-(2-hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

Participants

Reaction Steps

2-(4-Amino-3-iodo-phenyl)-ethanol (6.0 g, 23 mmol, 1.0 eq) was added to the solution of the 4,4,4-trifluoro-but-2-ynoic acid benzyl ester (5.7 g, 25 mmol, 1.1 eq) obtained from previous step in methanol (20 mL) at room temperature. The reaction mixture was stirred for 1 hour. After the solvent was removed, the residue was purified by flash chromatography (SiO2, hexanes-ethyl acetate) to yield 9.5 g of the desired enamine as pale yellow liquid (84.0% yield).

Provenance & Evidence