[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1.Br[CH2:16]/[CH:17]=[CH:18]\[CH3:19]>>[CH3:14][Si:2]([CH3:13])([CH3:1])[C:3]#[C:4][CH:5]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH2:16]/[CH:17]=[CH:18]\[CH3:19]Reaction of trimethyl(3-(tetrahydro-2H-pyran-2-yloxy)prop-1-ynyl)silane (0.157 g, 0.74 mmol) and (Z)-1-bromobut-2-ene (0.12 g, 0.89 mmol) according to General Procedure 11.A provided (Z)-trimethyl(3-(tetrahydro-2H-pyran-2-yloxy)hept-5-en-1-ynyl)silane. The (Z)-1-bromobut-2-ene starting material was synthesized in two steps according to General Procedures 11.F and 11.G.
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