Triphenylphosphine → 1-Methyl-1-[2-(trifluoromethyl)prop-2-en-1-yl]-1,2,3,4-tetrahydronaphthalene

To a solution of 1-iodo-2-(4-methylpent-4-en-1-yl)benzene (Intermediate 2) (8.3 g, 29 mmol), triphenylphosphine (1.57 g, 6 mmol), cuprous iodide (0.572 g, 3 mmol) and palladium acetate (0.673 g, 3 mmol) in anhydrous N,N-dimethylformamide (200 ml) was added tributyl[1-(trifluoromethyl)ethenyl]stannane (Intermediate 3) (14.5 g, 37.7 mmol). The flask was evacuated and filled with nitrogen four times and then placed in a bath preheated to 110° C. and stirred for 3 h. The mixture was allowed to cool, the solution was decanted from the black solid and concentrated to low volume. Heptane (200 ml) and water (200 ml) were added, insoluble material was filtered off, and the layers were separated. The aqueous layer was re-extracted with heptane (100 ml) and the combined organic layers were washed successively with water (2×200 ml), aqueous lithium chloride solution (200 ml), water (200 ml) and saturated brine (200 ml), dried over anhydrous sodium sulphate and evaporated. The resulting oil was purified by flash chromatography on an 800 g Biotage silica cartridge eluted with heptane to give the title compound (5.28 g, 72%).

1. customThe flask was evacuated
2. additionfilled with nitrogen four times
3. customplaced in a bath
4. custompreheated to 110° C.
5. temperatureto cool
6. customthe solution was decanted from the black solid
7. concentrationconcentrated to low volume
8. additionHeptane (200 ml) and water (200 ml) were added
9. filtrationinsoluble material was filtered off
10. customthe layers were separated
11. extractionThe aqueous layer was re-extracted with heptane (100 ml)
12. washthe combined organic layers were washed successively with water (2×200 ml), aqueous lithium chloride solution (200 ml), water (200 ml) and saturated brine (200 ml)
13. dry with materialdried over anhydrous sodium sulphate
14. customevaporated
15. customThe resulting oil was purified by flash chromatography on an 800 g Biotage silica cartridge
16. washeluted with heptane

ORD record

ord-bca504fca84147ee8bb5a4d220b43d88

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07902224B2