Diethyl Malonate → 2,2-Dicarboethoxy-indane

HRID 22509Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22509
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].Br[CH2:15][C:16]1[C:17]([CH2:22]Br)=[CH:18][CH:19]=[CH:20][CH:21]=1>O1CCCC1>[C:1]([C:2]1([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:22][C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15]1)([O:9][CH2:10][CH3:11])=[O:8]

Komponenten

5

Edukt 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydride2×HCID 66665o-Bis(bromomethyl)benzene

Produkt 1

HCID 110107772,2-Dicarboethoxy-indaneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

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%).

Aufarbeitung

  1. stirringstir for 16 hours
  2. temperaturewhile warming to room temperature
  3. filtrationFilter
  4. customevaporate the solvent in vacuo
  5. custompurify by silica gel chromatography (1:1 methylene chloride/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2ae85e72be7c4251ac9484b0d77503cb
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05428158

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