Hydrochloric Acid → HCID 86585746, compound

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%).

1. extractionthe mixture was extracted with ether
2. washThe organic layer was washed with water and brine
3. dry with materialdried on anhydrous sodium sulfate
4. customthe solvent was removed under reduced pressure
5. temperaturethe mixture was heated
6. temperatureto reflux for 1 h
7. extractionthe mixture was extracted with ethyl acetate
8. washThe organic layer was washed
9. washwashed with water and brine
10. dry with materialdried on anhydrous sodium sulfate
11. customthe solvent was removed under reduced pressure
12. customThe residue was purified by silica gel column chromatography (9:1 chloroform/acetonitrile)

ORD record

ord-3312038e854c44abbc4451a361ecd1e7

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06452014B1