Réaction #80728

Équation de réaction

4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-bromoquinoline

4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-bromoquinoline

Compound 24

4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-bromoquinoline

(trimethylsilyl)acetylene

→

title compound

4,4-Dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-[(trimethylsilyl)ethynyl]quinoline

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   AutreThe reaction mixture was degassed for an additional 5 min
2. 2
   AutreThe tube was sealed
3. 3
   ConcentrationThe reaction mixture was concentrated in vacuo
4. 4
   AutrePurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Mode opératoire

To a solution of 0.40 g (1.36 mmol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-1-iso-propyl-7-bromoquinoline (Compound 24) in 5.0 ml of triethylamine which was degassed under argon for 15 min in a sealable tube, were added successively 0.069 g (0.36 mmol) of copper(I)iodide, (1.0 ml, 7.1 mmol) of (trimethylsilyl)acetylene, and 0.147 g (0.21 mmol) of bis(triphenylphosphine)palladium(II) chloride. The reaction mixture was degassed for an additional 5 min. The tube was sealed and the reaction mixture was heated at 50° C. for 72 h. The reaction mixture was concentrated in vacuo. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as an oil. PNMR (CDCl3) d 0.25 (9H, s), 1.26 (6H, s), 1.54 (6H, d, J=7.1 Hz), 2.39 (2H, s), 4.60 (1H, p, J=7.1 Hz), 7.17 (3H, m).

Source