Reacción #1929026

Ecuación de reacción

(3-Iodopropyl)triethoxysilane

4-(Hydroxymethyl)phenyl benzoate

sodium hydride

→

title compound

Rendimiento 30.1%

4-((3-(Triethoxysilyl)propoxy)methyl)phenyl benzoate

Rendimiento 30.1%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooled in an ice bath
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   Temperaturathe mixture was refluxed for 36 hours
4. 4
   OtroThe reaction crude
5. 5
   Filtraciónwas filtered
6. 6
   Otrothe solvent was removed under reduced pressure
7. 7
   Otrothe resultant oil was chromatographed (hexane/ethyl acetate 8:2)

Procedimiento

4-(Hydroxymethyl)phenyl benzoate (1 g, 4.39 mmol) was dissolved in 20 mL of anhydrous tetrahydrofuran and cooled in an ice bath. A suspension of sodium hydride (60% suspension, 175 mg, 4.39 mmol) in 5 mL of anhydrous tetrahydrofuran was added dropwise under stirring. The resultant mixture was stirred at 0° C. for 1 hour. (3-Iodopropyl)triethoxysilane (1.46 g, 4.39 mmol) was added and the mixture was refluxed for 36 hours. The reaction crude was filtered, the solvent was removed under reduced pressure, and the resultant oil was chromatographed (hexane/ethyl acetate 8:2) thus affording 570 mg (1.32 mmol, yield=30%) of the title compound (HPLC purity=99.2%).

Fuente