Reaktion #74003

Reaktionsgleichung

hydrogen chloride

triethyleneglycol

Tert-butyl acrylate

sodium

→

tert-butyl 3-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)propanoate

Ausbeute 88.4%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.DISSOLUTIONhad dissolved
2. 2
   SonstigeAfter removal of the solvent
3. 3
   Extraktionextracted with 3×50 mL of ethyl acetate
4. 4
   WaschenThe combined organic layers were washed with saturated brine
5. 5
   Trocknendried over anhydrous sodium sulfate
6. 6
   SonstigeAfter evaporation of the solvent

Vorschrift

To triethyleneglycol (17.6 g, 117.20 mmol, 3.00 equiv) in anhydrous THF (70 mL), was added sodium (30 mg, 1.25 mmol, 0.03 equiv). Tert-butyl acrylate (5.0 g, 39.01 mmol, 1.00 equiv) was added after the sodium had dissolved. The resulting solution was stirred overnight at room temperature and then neutralized with 1.0 N hydrogen chloride. After removal of the solvent, the residue was suspended in 50 mL of brine and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with saturated brine and dried over anhydrous sodium sulfate. After evaporation of the solvent, the tert-butyl 3-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)propanoate (9.6 g) was isolated as a colorless oil, which was used directly for the next reaction step without further purification.

Quelle