Reacción #1605818

Ecuación de reacción

tert-butyldimethylchlorosilane

8-(3-Nitro-4-phenylphenoxy)octan-1-ol

imidazole

→

tert-butyldimethyl{[8-(3-nitro-4-phenylphenoxy)octyl]oxy}silane

Rendimiento 86.1%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurified water
2. 2
   workup.ADDITIONwas added
3. 3
   Otrothe reaction
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   LavadoThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
6. 6
   Secadoa saturated aqueous solution of ammonium chloride, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated under reduced pressure
8. 8
   OtroThe residue was purified by flash column chromatography

Procedimiento

8-(3-Nitro-4-phenylphenoxy)octan-1-ol (1.23 g, 3.5 mmol) and imidazole (408 mg, 6.0 mmol) were dissolved in tetrahydrofuran (15 mL) and a solution of tert-butyldimethylchlorosilane (750 mg, 5.0 mmol) in tetrahydrofuran (5 mL) was added thereto. After stirring the reaction mixture at room temperature for 18 hours, purified water was added to stop the reaction and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography to obtain tert-butyldimethyl{[8-(3-nitro-4-phenylphenoxy)octyl]oxy}silane (1.38 g).

Fuente