C[Al](C)C.[C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Si:18]([O:25][CH2:26][C:27]#[C:28][C:29](OCC)=[O:30])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl>[C:12]1([N:11]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:29](=[O:30])[C:28]#[C:27][CH2:26][O:25][Si:18]([C:21]([CH3:23])([CH3:22])[CH3:24])([CH3:20])[CH3:19])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1To a solution of 1.4 mL Me3Al (2.0M in hexanes) in 3.6 mL anhydrous CH2Cl2 under N2 was added 0.49 g of diphenylamine in one portion. After stirring 30 min, 0.35 g ethyl 4-(t-butyldimethylsilyloxy)-2-butynoate in 0.4 mL CH2Cl2 was added dropwise. The reaction was stirred overnight at room temperature, then heated in an oil bath at 35° overnight. The reaction was quenched by the addition of a few drops of 1N HCl, diluted with H2O, and extracted with CH2Cl2. The combined organics were with H2O and brine and dried over Na2SO4. Filtration, evaporation, and flash chromatography with a 10-15% Et2O/hexanes gradient provided 0.31 g of product.
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