Diethyl Malonate → HCID 21287874, compound

HRID 868249Notes

Reaction equation

HRID 868249 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]#[N:22].S([O-])(O)(=O)=O.[K+]>CN(C)C=O.O.C(OCC)(=O)C>[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])#[N:22]

Participants

8

Reactant 4

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 88737Heptanenitrile, 7-bromo-HCID 516920Potassium bisulfate

Product 1

HCID 21287874HCID 21287874, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.3 g of sodium hydride (as a 55% w/w dispersion in mineral oil) were gradually added with ice cooling to a solution of 8.0 ml of diethyl malonate dissolved in 80 ml of dimethylformamide. The mixture was stirred for 30 minutes, and then 10 g of 7-bromoheptanenitrile were added dropwise to it over a period of 30 minutes. The mixture was then stirred at room temperature for 20 hours in an atmosphere of nitrogen. At the end of this time, ethyl acetate and water were added to the mixture, which was then acidified by adding an aqueous solution of potassium hydrogen sulfate, after which the organic layer was separated. This layer was dried over anhydrous magnesium sulfate and the solvent was removed by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent: a 3:1 by volume mixture of cyclohexane and ethyl acetate) to afford 8.9 g of the title compound as a liquid.

Workup

  1. stirringThe mixture was then stirred at room temperature for 20 hours in an atmosphere of nitrogen
  2. customafter which the organic layer was separated
  3. dry with materialThis layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by evaporation under reduced pressure
  5. customThe residue was purified by column chromatography through silica gel (eluent
  6. additiona 3:1 by volume mixture of cyclohexane and ethyl acetate)

Sources & evidence

ORD record
ord-cbdff99f412346f1a3b4b00a946cec57
Source dataset
uspto-grants-1988_10
Patent number
US04778790

Reaction notes

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