Triphenylphosphine → 1-Ethyl-1-[2-(trifluoromethyl)-2-propen-1-yl]-1,2,3,4-tetrahydronaphthalene

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Reaction Steps

1-(4-Ethyl-4-penten-1-yl)-2-iodobenzene (Intermediate 11) (1.1 g, 3.66 mmole), tributyl[1-(trifluoromethyl)ethenyl]stannane (Intermediate 3) (1.4 g, 3.64 mmole), triphenyl phosphine (188 mg, 0.717 mmole), palladium acetate (82 mg, 0.365 mmole) and copper(I) iodide (69 mg, 0.362 mmole) were dissolved in dry DMF (60 ml). The solution was degassed by evacuating and filling the flask with nitrogen four times. The solution was then immediately immersed in a 110° C. oil bath, left to react for 3.5 h, cooled to room temperature then partitioned between water (100 ml) and cyclohexane (100 ml). The layers were separated and the aqueous layer was extracted with further cyclohexane (100 ml). The combined extracts were dried over anhydrous sodium sulphate and evaporated and the residue was applied to a silica Solid Phase Extraction (SPE) cartridge. Elution with cyclohexane gave the title compound (1.36 g) containing some residual impurities. This was used without additional purification.

Provenance & Evidence