Hydrochloric Acid → HCID 23577141, compound

Participants

Reaction Conditions

Reaction Steps

To the ethyl hydroxycinnamate (5.02 g, 22.1 mmol), prepared in Step 3, and pyridine (4.0 mL, 50.0 mmol) in dichloromethane (50 mL) at 0° C. under argon was added trifluoromethanesulfonic anhydride (4.0 mL, 23.7 mmol) over a 30-minute period. The mixture was stirred for 4 hours, warmed to 20° C., then worked-up (10% hydrochloric acid and 5% NaHCO3 washes) to afford ethyl (E)-3-chloro-4-(trifluoromethanesulfonyloxy)cinnamate as a white solid (7.90 g, 98% yield): m.p. 59-61° C.; Rf0.49 (20% ethyl acetate/hexane); 1H NMR spectrum (300 MHz, CDCl3) δ 1.35 (t, J=7.1 Hz, 3, CH3), 4.28 (q, J=7.1 Hz, 2, CH2), 6.45 (d, J=16.0 Hz, 1, HC═CCO), 7.38 (d, J=8.5 Hz, 1, ArH), 7.48 (dd, J=8.5, 1.8 Hz, 1, ArH), 7.59 (d, J=16.0 Hz, 1, C═CHCO), 7.67 ppm (d, J=1.9 Hz, 1, ArH).

Provenance & Evidence