Reaktion #50901

Reaktionsgleichung

Magnesium

3-chloropropyl vinyl ether

2-adamantanone

dibromoethane

→

2-Hydroxy-2-adamantylethyl Vinyl Ether

Lösungsmittel

water

H2SO4

tetrahydrofuran

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added to a round bottom flask
2. 2
   workup.ADDITIONcontaining the resulting mixture
3. 3
   workup.ADDITIONwere added drop-wise
4. 4
   SonstigeThen, the mixture was reacted for 2 hours
5. 5
   Temperaturthe resulting mixture was refluxed for 12 hours
6. 6
   ExtraktionThen, the organic layer was extracted from the reaction solution
7. 7
   Trocknendried with anhydrous sodium sulfate
8. 8
   SonstigeNext, after evaporating the solvent
9. 9
   Sonstigeto obtain an oily residue
10. 10
    Sonstigea rotary evaporator
11. 11
    Sonstigethe product was separated

Vorschrift

(Step-2) Magnesium metal(2.6 g) and anhydrous tetrahydrofuran (hereinafter referred to as THF(100 mL)) were added to a round bottom flask. Next, after dripping a small quantity of dibromoethane into the round bottom flask containing the resulting mixture to promote the reaction, 3-chloropropyl vinyl ether (12 g, 0.1 mol) and anhydrous THF(100 mL) were added drop-wise thereto. Then, the mixture was reacted for 2 hours. After dripping an adequate quantity of THF containing 2-adamantanone (15 g, 0.1 mol) in the mixture, the resulting mixture was refluxed for 12 hours. After the reaction was completed, the reaction mixture was slowly dissolved in excessive water and neutralized with thin H2SO4 solution. Then, the organic layer was extracted from the reaction solution using an adequate quantity of diethyl ether and then dried with anhydrous sodium sulfate. Next, after evaporating the solvent to obtain an oily residue using a rotary evaporator, the product was separated using a column chromatography method (hexane:ethyl acetate=3:1). (Yield: 60%)

Quelle