Reacción #69416

Ecuación de reacción

Chlorotriisopropylsilane

13

3-(2-Hydroxyethyl)benzaldehyde

1H-imidazole

→

desired compound

Rendimiento 96.0%

3-(2-((Triisopropylsilyl)oxy)ethyl)benzaldehyde

Rendimiento 96.0%

Disolventes

water

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   ExtracciónThe resulting mixture was extracted with diethyl ether
2. 2
   Lavadothe combined organic layers were washed with brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   Filtraciónfiltered
5. 5
   Otroevaporated
6. 6
   OtroThe residue was purified by silica gel column chromatography

Procedimiento

Chlorotriisopropylsilane (0.640 g, 0.71 mL, 3.3 mmol) was added dropwise to a 0° C. cooled solution of 13 (0.450 g, 3.0 mmol) and 1H-imidazole (0.410 g, 6.0 mmol) in anhydrous N,N-dimethylformamide (10 mL). The reaction mixture was stirred at 0° C. for 3 h and then diluted with water. The resulting mixture was extracted with diethyl ether, and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated. The residue was purified by silica gel column chromatography using ethyl acetate-hexanes 1:9 as eluent to furnish the desired compound as colorless oil. Yield: 96%.

Fuente