Réaction #1929026

Équation de réaction

(3-Iodopropyl)triethoxysilane

4-(Hydroxymethyl)phenyl benzoate

sodium hydride

→

title compound

Rendement 30.1%

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

Rendement 30.1%

Solvants

tetrahydrofuran

tetrahydrofuran

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source