Reacción #69427

Ecuación de reacción

2,2′-(1,3-Phenylene)diethanol

imidazole

Chlorotriisopropylsilane

→

desired compound

Rendimiento 35.0%

2-(3-(2-((Triisopropylsilyl)oxy)ethyl)phenyl)ethanol

Rendimiento 35.0%

Disolventes

N,N-dimethylformamide

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate (15 mL×2)
2. 2
   Lavadowashed with brine (10 mL×2)
3. 3
   SecadoThe organic layer was dried over anhydrous sodium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated to dryness
6. 6
   OtroThe residue so obtained
7. 7
   Otrowas purified by column chromatography
8. 8
   Lavadoeluting with 1:10 of ethyl acetate-hexanes

Procedimiento

2,2′-(1,3-Phenylene)diethanol (0.430 g, 2.59 mmol) and imidazole (0.176 g, 2.59 mmol) were dissolved in anhydrous N,N-dimethylformamide (15 mL) and cooled to 0° C. in an ice bath. Chlorotriisopropylsilane (0.22 mL) was slowly added and the reaction mixture was kept stirring at 0° C. for 3 h, and then diluted with water (5 mL), extracted with ethyl acetate (15 mL×2), and washed with brine (10 mL×2). The organic layer was dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The residue so obtained was purified by column chromatography eluting with 1:10 of ethyl acetate-hexanes to give the desired compound as a colorless oil. Yield 35%.

Fuente