(2,2-Dimethoxyethyl)(4-methoxyphenyl)sulfane → 5-Methoxy-1-benzothiophene

Under a nitrogen atmosphere, polyphosphoric acid (10 g) was added to anhydrous chlorobenzene (150 ml). To the resulting mixture, 1-(2,2-dimethoxyethylsulfanyl)-4-methoxybenzene (5.2 g, 22.7 mmol) was added under refluxing over 1.5 hours and the reaction mixture was heated to reflux overnight. The reaction was cooled to room temperature, and then the organic layer was separated. To the polyphosphoric acid layer, water was added and the obtained solution was extracted with methylene chloride. All organic layers thus obtained were washed with water and a saturated sodium chloride aqueous solution and dried with sodium sulfate. After filtration, the solvent was distilled under reduced pressure, and the obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:40)] to obtain the title compound (1.1 g, 30%).

1. temperatureunder refluxing over 1.5 hours
2. temperaturethe reaction mixture was heated
3. temperatureto reflux overnight
4. customthe organic layer was separated
5. additionTo the polyphosphoric acid layer, water was added
6. extractionthe obtained solution was extracted with methylene chloride
7. customAll organic layers thus obtained
8. washwere washed with water
9. dry with materiala saturated sodium chloride aqueous solution and dried with sodium sulfate
10. filtrationAfter filtration
11. distillationthe solvent was distilled under reduced pressure
12. customthe obtained residue was purified by silica gel column chromatography [developing solution=ethyl acetate:n-hexane (1:40)]

ORD record

ord-d27dc457d73f45a28cb4256efd46701c

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943748B2