Benzyl acetoacetate → (E)-3-[4-(2-Hydroxy-ethyl)-2-iodo-phenylamino]-but-2-enoic Acid Benzyl Ester

Participants

Reaction Steps

To a solution of 4-amino-3-iodophenethyl alcohol from Step A (10 g, 38 mmol) and benzyl acetoacetate (7.3 g, 38 mmol) in benzene (150 mL) was added p-toluenesulfonic acid (361 mg, 1.9 mmol). The mixture was heated at reflux overnight using a Dean Stark condenser. The mixture was washed with water and brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to give 16.6 g (99%) of the crude desired product as a light brown oil: MS(APCI+): m/z 438.1 (MH+). The compound was taken to Step C without further purification.

Provenance & Evidence