Diethyl Malonate → 2,2-Dicarboethoxy-indane

HRID 2395989Notes

Reaction equation

HRID 2395989 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 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-dicarboethoxy-indan (9.64 g, 74%).

Workup

  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)

Sources & evidence

ORD record
ord-d11576f4ba8c420395677bf6e9ea6dcf
Source dataset
uspto-grants-1996_02
Patent number
US05491141

Reaction notes

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