Reaktion #50787

Reaktionsgleichung

sodium hydride

sodium hydride

diethyl malonate

α,α'-dibromo-o-xylene

→

2,2-dicarboethoxyindan

Ausbeute 74.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstir for 16 hours
2. 2
   Temperaturwhile warming to room temperature
3. 3
   FiltrationFilter
4. 4
   Sonstigeevaporate the solvent in vacuo
5. 5
   Sonstigepurify by silica gel chromatography (1:1 methylene chloride/hexane)

Vorschrift

Dissolve diethyl malonate (7.6 mL, 50 mmol) in anhydrous tetrahydrofuran (500 mL) and place under an argon atmosphere. Cool to 5° C., add sodium hydride (1.2 g, 50 mmol) and stir briefly until homogeneous. Add α,α'-dibromo-o-xylene (13.2 g, 50 mmol) and stir an additional 15 minutes. Add additional sodium hydride 1.2 g, 50 mmol) and stir for 16 hours while warming to room temperature. Filter, evaporate the solvent in vacuo and purify by silica gel chromatography (1:1 methylene chloride/hexane) to give 2,2-dicarboethoxyindan (9.64 g, 74%).

Quelle