Reaction #1929026

Reaction equation

(3-Iodopropyl)triethoxysilane

4-(Hydroxymethyl)phenyl benzoate

sodium hydride

→

title compound

Yield 30.1%

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

Yield 30.1%

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

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

Procedure

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