反応 #79441

反応方程式

1,2,3,4-tetrahydro-4,4,6-trimethyl-1-oxo-7-bromonaphthalene

Lithium chloride

ethyl 4-(1-(tributylstannyl)-2-(trimethylsilyl)-ethen-1-yl)-benzoate

→

title material

Ethyl 4-[1-(5,6,7,8-tetrahydro-3,5,5-trimethyl-8-oxo-2-naphthalenyl)-2-trimethylsilyl -ethenyl]benzoate

反応条件

後処理

1. 1
   その他the resulting mixture was again purged with argon
2. 2
   温度cooled to room temperature
3. 3
   workup.ADDITIONThe mixture was poured into cold water (1 L)
4. 4
   workup.ADDITIONwas diluted with ethyl ether
5. 5
   その他The organic phase was separated
6. 6
   洗浄washed with cold water (2×1 L), saturated sodium bicarbonate (1 L), brine
7. 7
   乾燥dried over anhydrous magnesium sulfate
8. 8
   ろ過filtered
9. 9
   濃縮concentrated
10. 10
    その他The residue was purified by silica gel chromatography (8×15 cm, 0 to 5% ethyl acetate/toluene)

実験手順

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%).

出典