1,2-Dichloroethane → HCID 68191111, compound

Participants

Reaction Conditions

Reaction Steps

To a 20 mL vial was added a solution of methyl (2Z)-3-(4-chlorophenyl)-2-[(5-pyridin-4-yl-2-thienyl)carbonyl]acrylate (0.049 g, 0.128 mmol), in 1,2-dichloroethane (4.000 mL, 50.77 mmol). Aluminum trichloride (0.0340 g, 0.255 mmol) was added and the reaction mixture was heated to 80° C. and allowed to stir for 2 days. The reaction was cooled to ambient temperature and quenched by the addition of a saturated aqueous solution of sodium bicarbonate (5.00 mL) and extracted with EtOAc (10.00 mL×3). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was dry loaded onto silica gel and then purified using ISCO (12 g cartridge, gradient hexanes to 100% EtOAc over 30 min) to afford the title compound (0.022 g, 43%) as a yellow oil. LC/MS (AA) ES+ 384, 386. 1H NMR (dmso-d6, 400 MHz): δ 8.66-8.65 (m, 2H), 7.81-7.78 (m, 3H), 7.45-7.34 (m, 4H), 4.96 (d, 1H), 4.13 (d, 1H), 3.72 (s, 3H).

Provenance & Evidence