Réaction #1322

Équation de réaction

6-ethynyl-1,2,3,4-tetrahydro-4,4-dimethylnaphthalen-1-one

6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

Compound K

6-ethynyl-3,4-dihydro-4,4-dimethylnaphthalen-1(2H)-one

ethyl 4-iodobenzoate

→

title compound

Ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-2-yl)ethynyl]benzoate

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   AutreThe solution mixture was flushed with argon for 5 minutes
2. 2
   FiltrationThe reaction mixture was filtered through celite
3. 3
   Concentrationthe filtrate concentrated in vacuo
4. 4
   AutrePurification by flash chromatography (silica, 10% EtOAc-hexane)

Mode opératoire

To a solution of 8.8 g (47.8 mmol) of 6-ethynyl-1,2,3,4-tetrahydro-4,4-dimethylnaphthalen-1-one (Compound K) flushed for 15 minutes with a stream of argon, and 13.2 g (47.8 mmol) of ethyl 4-iodobenzoate in 200 ml of triethylamine was added 1.1 g (1.6 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.30 g (1.6 mmol) of cuprous iodide. The solution mixture was flushed with argon for 5 minutes and then stirred at ambient temperature for 18 hours. The reaction mixture was filtered through celite and the filtrate concentrated in vacuo. Purification by flash chromatography (silica, 10% EtOAc-hexane) yielded the title compound as a white solid.

Source