9-Borabicyclo(3.3.1)nonane → Ethyl(2S)-2-ethoxy-3-[4-(2-hydroxyethyl)phenyl]propanoate

Beteiligte Stoffe

Reaktionsschritte

9-BBN (3.0 mmol, 6 mL of a 0.5 M solution in hexanes) was added to a stirred solution of ethyl(2S)-2-ethoxy-3-(4-vinylphenyl)propanoate (0.37 g, 1.48 mmol) in dry THF under argon. The reaction mixture was stirred for 22 h under argon. Trimethylamine N-oxide dihydrate (0.60 g, 5.4 mmol) was added and the mixture was heated to reflux overnight and diluted with ether (50 mL). The organic layer was washed with brine (×3), dried (MgSO4), filtered, and evaporated. The crude product was purified by flash chromatography (silica, heptane/ethyl acetate 3:1) to give the title compound as an colorless oil (0.24 g, 62%).

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