Реакция #1336

Уравнение реакции

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

Растворители

THF

Условия реакции

Обработка

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

Методика

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.

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