[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]#[C:4]B1C2CCCC1CCC2.C([O:18][CH2:19][CH3:20])C.CO.[CH2:23]([CH2:25]N)O.[CH3:27][CH2:28][CH2:29][CH2:30]C>>[CH3:1][Si:2]([CH3:14])([CH3:15])[C:3]#[C:4][CH:19]([OH:18])[CH2:20][CH2:27][CH2:28][CH2:29][CH2:30][CH2:23][CH3:25]Dissolve B-(2-(trimethylsilyl)ethynyl)-9-borabicyclo[3.3.1]nonane.tetrahydrofuran complex (2.4 g, 8.3 mmol) in pentane (25 mL) and add octyladldehyde (1.3 mL, 8.3). Stir at room temperature for 40 minutes and evaporate the solvent under a positive pressure of nitrogen to give a yellow solid. Add ethyl ether (30mL) and methanol (336 μL, 8.3 mmol), cool to 0° C. and add, by dropwise addition, ethanolamine (0.5 mL, 8.3 mmol). Stir overnight, centrifuge the reaction mixture and separate the clear supernatant liquid. Wash the precipitate with pentane (2×25 mL) and combine the organic phase. Wash with water (2×25 mL) and dry (MgSO4). Evaporate the solvent in vacuo and purify by silica gel chromatography (19:1 hexane/ethyl acetate) to give the title compound as a clear liquid (1.71 g, 91%).
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