Reacción #1336

Ecuación de reacción

trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate

Compound 117

trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate

tetrabutyl ammonium fluoride

→

title compound

4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxymethylnaphth-2-yl)ethynyl]benzoic acid

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónconcentrated in vacuo to an oil
2. 2
   workup.ADDITIONslowly diluted with water
3. 3
   Extracciónextracted with Et2O
4. 4
   SecadoThe organic layer was dried over Na2SO4
5. 5
   Concentraciónconcentrated in vacuo to an oil
6. 6
   Otropurified by flash chromatography (silica, 90% EtOAc-hexane)

Procedimiento

To a solution of 0.25 g (0.49 mmol) of trimethylsilylethyl 4-[(5,6,7,8-tetrahydro-5-hydroxy-8,8-dimethyl-5-carboethoxy-methylnaphth-2-yl)ethynyl]benzoate (Compound 117) in 5 ml of dry THF (flushed with argon) was added 1.48 ml (1.5 mmol) of tetrabutyl ammonium fluoride (1M solution in THF). The reaction mixture was stirred at room temperature for 12 hours, concentrated in vacuo to an oil and slowly diluted with water. The solution was acidified to pH 4 with 10% HCl and extracted with Et2O. The organic layer was dried over Na2SO4, concentrated in vacuo to an oil and purified by flash chromatography (silica, 90% EtOAc-hexane) to give the title compound as a white solid.

Fuente