反応 #6652

反応方程式

trimethylsilylacetylene

4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline

Compound 94

4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline

methylene chloride

→

title compound

4,4-Dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline

溶媒

triethylamine

反応条件

後処理

1. 1
   その他The mixture was degassed again under argon
2. 2
   その他the tube was sealed
3. 3
   workup.ADDITIONwas added to the reaction mixture
4. 4
   ろ過the mixture filtered
5. 5
   濃縮The filtrate was concentrated in vacuo
6. 6
   その他the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

実験手順

A solution of 1.608 g (6.7 mmol) of 4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline (Compound 94) in 1.5 ml of triethylamine in a heavy-walled tube was degassed under argon and then treated with 75 mg (0.39 mmol) of cuprous iodide and 150 mg (0.21 mmol) of bis(triphenylphosphine) palladium (II) chloride. The mixture was degassed again under argon, treated with 2.09 g (21.2 mmol) of trimethylsilylacetylene and the tube was sealed. The mixture was heated at 50 degrees C. for 48 h. After cooling to room temperature methylene chloride was added to the reaction mixture and the mixture filtered. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a yellow oil. PMR (CDCl3): δ 0.20 (9H, s), 1.20 (6H, s), 1.57-1.63 (2H, m), 3.16-3.25 (2H, m), 4.02 (1H, broad s), 6.24 (1H, d, J~8.2 Hz), 7.00 (1H, dd, J~8.2 Hz, 1.8 Hz), 7.26 (1H, d, J~1.8 Hz).

出典