Lithium Chloride → HCID 54456954, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 1,2,3,4-tetrahydro-4,4,6-trimethyl-1-oxo-7-bromonaphthalene (8.5 g, 31.8 mmol) was purged with argon (2×). Lithium chloride (4.0 g), copper iodide (0.860 g), tetrakis(triphenylphosphine)palladium(0) (1.8 g, 1.6 mmol) and ethyl 4-(1-(tributylstannyl)-2-(trimethylsilyl)-ethen-1-yl)-benzoate (24.0 g, 44.5 mmol) were then added and the resulting mixture was again purged with argon. The mixture was heated to 80° C. for ˜4 hours, and then cooled to room temperature. The mixture was poured into cold water (1 L) and was diluted with ethyl ether. The organic phase was separated, washed with cold water (2×1 L), saturated sodium bicarbonate (1 L), brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene) to give the title material which was triturated in hexane (12.2 g, 88%).

Provenance & Evidence