N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline → N-((6-(5-(But-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)(phenyl)methyl)-2,6-diisopropylaniline

Participants

Reaction Steps

In the glovebox, N-((6-(5-(but-3-enyloxy)-2,4-dimethylphenyl)pyridin-2-yl)methylene)-2,6-diisopropylaniline (1.527 g, 3.40 mmol) is dissolved in toluene (40 mL). Phenylmagnesiumbromide (3.0M in ether, 1.36 mL, 4.09 mmol) is added, and the reaction mixture stirred at room temperature for one hour, removed from the glovebox, and quenched by addition of water (60 mL), and ether (80 mL). The aqueous layer is washed with additional ether (40 mL), and the combined organic fractions are washed with brine, dried over magnesium sulfate and filtered. Solvents are removed in vacuo, and the crude product is purified by column chromatography using 10:1 hexanes:ethylacetate (Rf=0.39) to yield 1.27 g (72.0%) of a very pale yellow solid. The structure is assigned by 1H NMR as shown in FIG. 1.

Provenance & Evidence