Reaktion #69416

Reaktionsgleichung

Chlorotriisopropylsilane

13

3-(2-Hydroxyethyl)benzaldehyde

1H-imidazole

→

desired compound

Ausbeute 96.0%

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

Ausbeute 96.0%

Lösungsmittel

water

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe resulting mixture was extracted with diethyl ether
2. 2
   Waschenthe combined organic layers were washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

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%.

Quelle