Tributylstannane → 4-(Tributylstannyl)but-3-en-1-ol

Participants

Reaction Conditions

Reaction Steps

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%).

Provenance & Evidence