Реакция #6652

Уравнение реакции

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

Растворители

triethylamine

Условия реакции

Обработка

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

Методика

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).

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