Реакция #50787

Уравнение реакции

sodium hydride

sodium hydride

diethyl malonate

α,α'-dibromo-o-xylene

→

2,2-dicarboethoxyindan

Выход 74.0%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGstir for 16 hours
2. 2
   Температураwhile warming to room temperature
3. 3
   ФильтрацияFilter
4. 4
   Другоеevaporate the solvent in vacuo
5. 5
   Другоеpurify by silica gel chromatography (1:1 methylene chloride/hexane)

Методика

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%).

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