Tetrahydrofuran → HCID 68183095, compound

Participants

Reaction Conditions

Reaction Steps

To a 100 mL round bottom flask was added a suspension of sodium hydride (0.1574 g, 3.936 mmol) in tetrahydrofuran (16.000 mL, 197.26 mmol). Dimethyl carbonate (0.663 mL, 7.872 mmol) was added followed by 1-(5-pyridin-4-yl-2-thienyl)ethanone (0.400 g, 1.968 mmol) which was added in portions. The red reaction mixture was heated to 60° C. and allowed to stir for 18 hours. The reaction was cooled to ambient temperature and quenched by the dropwise addition of water (5.00 mL). The mixture was neutralized to pH 7 by the addition of a saturated aqueous solution of ammonium chloride (10.00 mL) and extracted with EtOAc (70.00 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% EtOH over 30 min) to afford the title compound (0.197 g, 36%) as a yellow oil. LC/MS (AA) ES+ 262. 1H NMR (dmso-d6, 400 MHz): δ 8.67-8.65 (m, 2H), 8.08 (d, 1H), 7.94 (d, 1H), 7.78-7.77 (m, 2H), 4.20 (s, 2H), 3.67 (s, 3H).

Provenance & Evidence