Dimethylformamide → HCID 18472473, compound

Under nitrogen atmosphere, to a solution of 5-[5-(4-methylphenyl)thiophen-2-yl]valeric acid (2.60 g) in tetrahydrofuran (30 ml) was added oxalyl chloride (1.24 ml) at room temperature and then a drop of DMF, and the mixture was stirred 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was dissolved in dichloromethane (30 ml). To the mixture was added tin tetra-chloride (1.5 ml) at 0° C., and the mixture was stirred at room temperature for 3 hours. The reaction mixture was added to water to stop the reaction, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:9→1:5) to give 2-(4-methylphenyl)-4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene (2.07 g) as pale yellow crystals.

1. customUnder reduced pressure, the solvent was evaporated
2. dissolutionthe residue was dissolved in dichloromethane (30 ml)
3. additionTo the mixture was added tin tetra-chloride (1.5 ml) at 0° C.
4. additionThe reaction mixture was added to water
5. customthe reaction
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic layer was washed with saturated sodium chloride solution
8. dry with materialdried with magnesium sulfate
9. concentrationconcentrated under reduced pressure
10. customThe residue was separated
11. custompurified with column chromatography (ethyl acetate/hexane=1:9→1:5)

ORD record

ord-ee78e2f7d0af428a9dcc5b75ddd08883

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268354B1