Réaction #1331

Équation de réaction

chlorotrimethylsilane

ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

Compound 9

ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate

triethylamine

→

title compound

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

Solvants

CH2Cl2

Conditions de réaction

Traitement

1. 1
   AutreThe solution was flushed with nitrogen
2. 2
   Autre(flushed with nitrogen) for 30 minutes
3. 3
   Concentrationconcentrated in vacuo to an oil
4. 4
   Autrepurified by flash chromatography (silica, 10% EtOAc-hexane)

Mode opératoire

To a solution of 0.23 g (0.54 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethylnaphth-2-yl)ethynyl]benzoate (Compound 9) in 4 ml of dry CH2Cl2 was added 0.06 ml of triethylamine (0.81 mmol). The solution was flushed with nitrogen and then 0.12 g (0.81 mmol) of chlorotrimethylsilane was slowly added by syringe. The mixture was stirred at room temperature (flushed with nitrogen) for 30 minutes, concentrated in vacuo to an oil and purified by flash chromatography (silica, 10% EtOAc-hexane) to yield the title compound as a clear oil.

Source