Реакция #10712

Уравнение реакции

Catechol

Diethyl dibromomalonate

potassium carbonate

→

benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester

Выход 73.2%

Растворители

acetone

Условия реакции

Обработка

1. 1
   ДругоеThe solvent was removed under reduced pressure, and water
2. 2
   workup.ADDITIONwas added to the residue
3. 3
   ЭкстракцияThe residue was extracted with dichloromethane
4. 4
   Промывкаthe organic phase was washed with brine
5. 5
   Сушкаdried over magnesium sulfate
6. 6
   Другоеevaporated

Методика

Ex-1A: Catechol (2.2 g, 20 mmol) was dissolved in acetone. Diethyl dibromomalonate (7.0 g, 22 mmol) and potassium carbonate (2.76 g) were added, and the mixture was stirred at room temperature overnight. The solvent was removed under reduced pressure, and water was added to the residue. The residue was extracted with dichloromethane, and the organic phase was washed with brine, dried over magnesium sulfate and evaporated. Chromatography (hexanes/ethyl acetate, 4:1) gave 3.9 g of benzo[1,3]dioxole-2,2-dicarboxylic acid diethyl ester. 1H-NMR (CDCl3) δ 6.90–6.97 (m, 4H), 4.37 (q, J=7 Hz, 4H), 1.32 (t, J=7 Hz, 6H).

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