Hexane → (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane

In a nitrogen atmosphere, (5-methyl-2-thienylethynyl)trimethylsilane (1.0 g, 5.2 mmol) was added to a hexane solution (1.0 mol/L) containing diisobutylaluminum (6.0 ml, 6.0 mmol), followed by stirring at room temperature for 24 hours. The mixture was added to a tetrahydrofuran solution, which contained Pd(PPh3)4 (0.3 g, 0.26 mmol), zinc chloride (1.0 g, 7.3 mmol), and p-methoxyiodobenzene (1.7 g, 7.3 mmol), and which had independently been prepared in another container, followed by stirring in an nitrogen atmosphere at 65° C. for 24 hours. The solution obtained was cooled to room temperature, and water was then added thereto, followed by extraction with chloroform. The organic layer was washed with a saturated sodium chloride solution and then dried with magnesium sulfate, followed by filtration. The filtrate was concentrated using a rotary evaporator. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1). Thus, (Z)-(1-(4-methoxyphenyl)-2-(5-methyl-2-thienyl)-ethenyl)trimethylsilane (1.0 g, 3.44 mmol) was obtained in a yield of 66%.

1. customhad independently been prepared in another container
2. stirringby stirring in an nitrogen atmosphere at 65° C. for 24 hours
3. customThe solution obtained
4. temperaturewas cooled to room temperature
5. extractionfollowed by extraction with chloroform
6. washThe organic layer was washed with a saturated sodium chloride solution
7. dry with materialdried with magnesium sulfate
8. filtrationfollowed by filtration
9. concentrationThe filtrate was concentrated
10. customa rotary evaporator
11. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

ORD-Eintrag

ord-b755e3dbace041b5a77266796b14546e

Quelldatensatz

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08436173B2