[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[CH3:6][CH2:7][CH2:8][CH2:9][SnH:10]([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:11][CH2:12][CH2:13][CH3:14]>CC(N=NC(C#N)(C)C)(C#N)C.CCOC(C)=O>[CH2:15]([Sn:10]([CH2:9][CH2:8][CH2:7][CH3:6])([CH2:11][CH2:12][CH2:13][CH3:14])[CH:4]=[CH:3][CH2:2][CH2:1][OH:5])[CH2:16][CH2:17][CH3:18]A stirred mixture of but-3-yn-1-ol (7.00 g, 99.87 mmol) and AIBN (0.50 g, 2.81 mmol), contained in large round-bottomed flask equipped with a reflux condenser, was degassed with N2 at 25° C. and treated with Bu3SnH (40.4 mL, 150 mmol). The mixture was slowly heated to 90° C. and stirred at 100° C. for 16 hours. The solution was cooled and the crude product was subjected to chromatography on Al2O3 gel with a 1-10% gradient of EtOAc in PE. The mixture of E-isomer and Z-isomer were obtained as colorless oil (15 g, 40.9%).
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