2-Naphthalenecarboxaldehyde → HCID 178450056, compound

Temperature

-78 °C

4-Bromo-1H-imidazole (1.95 g) was dissolved in THF (30 ml), and the solution was cooled to −78° C. To the solution was added a solution of t-butyllithium in pentane (1.7 M; 20 ml). The mixture was stirred at 0° C. for 1.5 h. The mixture was again cooled to −78° C., and a solution of 2-formylnaphthalene (3.32 g) in THF (20 ml) was added. After the temperature was elevated from −78° C. to room temperature, the mixture was stirred at room temperature for 16 h. To the mixture was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The residue was purified by silica gel column chromatography,(eluent, dichloromethane:methanol=10:1). Recrystallization from dichloromethane-methanol gave the titled compound (1.00 g) as a colorless solid.

1. temperatureThe mixture was again cooled to −78° C.
2. customwas elevated from −78° C. to room temperature
3. stirringthe mixture was stirred at room temperature for 16 h
4. extractionthe mixture was extracted with ethyl acetate
5. customThe organic layer was dried
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography,(eluent, dichloromethane
8. customRecrystallization from dichloromethane-methanol

ORD record

ord-615eea60345041cda709cc79aa448a98

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06573289B1