Vinyl Chloride → HCID 54246246, compound

Participants

Reaction Steps

Degassed anhydrous tetrahydrofuran (500 mL) was added to 5.86 g (4.32 mmol) solid tetrakis(triphenylphosphine) palladium(0) and copper (I) iodide (5.17 g, 27.1 mmol) stirring under argon. A solution of the vinyl chloride (compound M of step (a) 45.38 g, 226.1 mmol) in 100 mL of dry tetrahydrofuran was added via cannula followed immediately by the addition of 45 mL (455 mmol) neat butylamine. The flask was wrapped in aluminum foil to exclude light and then 41.6 mL (294 mmol) of trimethylsilyl acetylene was added via syringe over 4 min. After about 10 min the reaction became very warm and was cooled in an ice water bath for 3 min. The cooling bath was then removed and the reaction allowed to stir for 4 h at ambient temperature. Air was bubbled through the reaction for 15 min and then the reaction was filtered by suction through a glass frit using pentane then ether washes for transfer. The reaction was diluted with ether and washed with five 500 ml portions of water. The aqueous washes were reextracted with a small amount of diethyl ether and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated on a rotary evaporator. Flash chromatography over SiO2 using 2.5% to 4% ethyl acetate/hexane as eluent provided 52.86 g (89%) of liquid as the desired product:

Provenance & Evidence