Hydrochloric Acid → HCID 86585746, compound

Participants

Reaction Steps

To a solution of 2-bromo-5-dimethoxymethylfuran (273 mg, 1.24 mmol) in tetrahydrofuran (7 mL) w e re added n-BuLi (1.6 mol/L in hexane; 1.6 ml, 2.5 mmol) and dimethylformamide (0.25 mL, 3.0 mmol) at −78° C. under nitrogen atmosphere, and the mixture was stirred for 10 min. Water was added and the mixture was extracted with ether. The organic layer was washed with water and brine, dried on anhydrous sodium sulfate, and the solvent was removed under reduced pressure. To the residue were added ethanol (8 mL), 2,4-thiazolidinedione (129 mg, 1.1 mmol), and piperidine (0.092 mL, 0.92 mmol), and the mixture was heated to reflux for 1 h. Water and hydrochloric acid (1 mol/L; 1 mL) were added, and the mixture was extracted with ethyl acetate. The organic layer was washed washed with water and brine, dried on anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (9:1 chloroform/acetonitrile) gave 5-[(5-dimethoxymethyl-2-furanyl)methylene]-2,4-thiazolidinedione (91 mg, 2 steps 27%).

Provenance & Evidence