1-Butanol → 3-(3-Thienyl)pyridine

Temperature

100 °C

Into a glass reaction vessel equipped with a cooling apparatus were added 0.015 mmol of bis(dicyclopentyl(2-methoxyphenyl)phosphine)dichloropalladium(II), 1.5 mmol of 3-bromopyridine, 2.25 mmol of 3-thiopheneboronic acid, 3.0 mmol of potassium phosphate and 4 mL of n-butanol. The resultant mixture was stirred with heating at 100° C. for 4 hours. The resultant reaction mixture was cooled down to room temperature, 20 mL of water was added, and the mixture was extracted with 20 mL of diethyl ether twice. The resultant organic layers were mixed, and dried over anhydrous magnesium sulfate, then, filtrated, to obtain a solution. This solution was concentrated, and purified by silica gel column chromatography, to obtain 3-(3-thienyl)-pyridine with a yield of 92%.

1. customInto a glass reaction vessel
2. customequipped with a cooling apparatus
3. customThe resultant reaction mixture
4. temperaturewas cooled down to room temperature
5. extractionthe mixture was extracted with 20 mL of diethyl ether twice
6. additionThe resultant organic layers were mixed
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltrated
9. customto obtain a solution
10. concentrationThis solution was concentrated
11. custompurified by silica gel column chromatography

ORD record

ord-1f186d8ed4054494bf2368eccc09dfbe

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238665B2