반응 #6652

반응 방정식

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

용매

triethylamine

반응 조건

후처리

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

실험 절차

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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