Water → HCID 86706805, compound

Under a nitrogen atmosphere, 3-methoxythiophene (5.0 g, 44.8 mmol), 2-butyloctanol (16.7 g, 89.6 mmol), and p-toluenesulfonic acid (850 mg, 4.48 mmol) were dissolved in toluene (40 ml), and refluxing was performed for 15 hours. Then, water was added to the reaction solution. The reaction solution was then extracted with methylene chloride, and an organic layer was washed with a saturated saline solution and water. The organic layer was dried with anhydrous magnesium sulfate, and, after filtration, the solution was distilled off under reduced pressure. By separating and purifying the obtained reaction solution by silica gel column chromatography in which hexane was used as a mobile phase, a target substance was obtained as clear oil (83% yield). 1H-NMR (400 MHZ, CDCl3, TMS) δ 7.17 (dd, J=5.2 Hz, 1.6 Hz, 1 H), 6.76 (d, J=5.2 Hz, 1 H), 6.21 (d, J=1.6 Hz, 1 H), 3.81 (d, J=5.8 Hz, 2 H), 1.25 (m, 17 H), 0.88 (m, 6 H)

1. temperaturerefluxing
2. extractionThe reaction solution was then extracted with methylene chloride
3. washan organic layer was washed with a saturated saline solution and water
4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
5. filtrationafter filtration
6. distillationthe solution was distilled off under reduced pressure
7. customBy separating
8. custompurifying
9. customthe obtained reaction solution by silica gel column chromatography in which hexane

ORD record

ord-bf2824e04beb47b4bf0f2e6830cd983c

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09312491B2