Réaction #1605818

Équation de réaction

tert-butyldimethylchlorosilane

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

imidazole

→

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

Rendement 86.1%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autrepurified water
2. 2
   workup.ADDITIONwas added
3. 3
   Autrethe reaction
4. 4
   Extractionthe mixture was extracted with ethyl acetate
5. 5
   LavageThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
6. 6
   Séchagea saturated aqueous solution of ammonium chloride, and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by flash column chromatography

Mode opératoire

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).

Source