Acetic Anhydride → HCID 178471956, compound

Participants

Reaction Steps

A solution of ethyl 3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate (3.09 g, 11.7 mmol), Ac2O (6.7 mL, 70.9 mmol) and triethyl orthoformate (3.90 mL, 23.5 mmol) was heated at 120° C. for 3 hours. The mixture was concentrated in vacuo and dried under high vacuum. The crude product was dissolved in anhydrous tolene (40 mL) and (1-amino-cyclopropyl)-ethanol (1.82 g, 11.7 mmol) was added very slowly at 0° C. The ration mixture was stirred at room temperature for 5 hours and diluted with toluene. The organic layer was washed with water, brine, and then dried. The solvent was removed by evaporation and the crude product was purified by column chromatography (Hexane:EtOAc 2:1→1:1) to yield the title compound (2.99 g, 68%) as a yellow oil. 1H-NMR (400 MHz, CDCl3) δ 0.85-0.92 (2H, m), 0.94-1.11 (5H, m), 1.85-1.91 (2H, m), 3.85-3.89 (2H, m), 3.99-4.09 (2H, m), 6.95-7.13 (1H, m), 8.19 (1H, d, J=14.1 Hz), 9.84, 11.2 (each d, J=13.4 Hz, total 1H). EIMS (+) 375 [M]+.

Provenance & Evidence