Dimethylformamide → HCID 18472473, Verbindung

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-cyclo-hepta[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-Eintrag

ord-f5dd77d5177249169ace49b2f4a1e0d1

Quelldatensatz

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06413947B1