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

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Reaction Steps

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%).

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