Reaktion #1336

Reaktionsgleichung

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

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle