Diethyl Malonate → 2,2-Dicarboethoxy-indane

HRID 2395972Notes

Reaction equation

HRID 2395972 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 110107772,2-Dicarboethoxy-indaneYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

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 additional15 minutes. Add additional sodium hydride (1 .2 g, 50 mmol) and stir for 16hours 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%).

Workup

  1. stirringstir for 16hours
  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)

Sources & evidence

ORD record
ord-73581964123242c79fb7e5798a7f9835
Source dataset
uspto-grants-1996_02
Patent number
US05491142

Reaction notes

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