B(F)(F)F.CCOCC.[C:10]([C:14]1[CH:15]=[C:16]([C:20]2(O)[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]2)[CH:17]=[CH:18][CH:19]=1)([CH3:13])([CH3:12])[CH3:11].[N:28]([Si](C)(C)C)=[N+:29]=[N-:30].C(OCC)(=O)C>C(OCC)C.[Cl-].[NH4+]>[N:28]([C:20]1([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:15]=2)[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]1)=[N+:29]=[N-:30]Borontrifluoride-etherate (2.0 mL, 15.7 mmol) was added to a solution of 1-(3-tert-butyl-phenyl)-4-methylene-cyclohexanol (3.60 g, 14.7 mmol) and azidotrimethylsilane (4.0 mL, 30.1 mmol) in diethyl ether (30 mL) and placed into a preheated oil bath at 45° C. After heating at reflux for 4 h, the solution was diluted with saturated aqueous ammonium chloride and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 99:1, 49:1, and 24:1 hexanes:ethyl acetate as the eluant to yield 1.46 g (37% yield) of 1-(1-azido-4-methylene-cyclohexyl)-3-tert-butyl-benzene as a clear oil.
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