Diethyl Malonate → HCID 15097258, compound

HRID 329522Notes

Reaction equation

HRID 329522 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[Na].Br[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29]>C(O)C>[CH3:29][O:28][CH2:27][CH2:26][O:25][CH2:24][O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 7761Diethyl MalonateHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 150972571-Bromo-5-(2-methoxyethoxy)methoxypentane

Product 1

HCID 15097258HCID 15097258, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 37.80 of diethyl malonate dissolved in 20 ml of absolute ethanol was added dropwise to a solution of sodium ethoxide prepared by gradually adding 3.00 g of metallic sodium to 30 ml of absolute ethanol. To the mixture was added a solution of 30.01 g of 1-bromo-5-(2-methoxyethoxy)methoxypentane (prepared as described in Preparation 60) dissolved in 10 ml of absolute ethanol. The mixture was heated under reflux for 21 hours, after which it was allowed to cool, and then the solvent was distilled off. The residue was mixed with water, and the mixture was extracted three times with ethyl acetate. The combined extracts were washed with water, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 850 g of silica gel, and 32.78 g of the title compound were obtained, as a colorless oil, from those fractions eluted with a 4:1 by volume mixture of hexane and ethyl acetate.

Workup

  1. customprepared
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 21 hours
  4. temperatureto cool
  5. distillationthe solvent was distilled off
  6. additionThe residue was mixed with water
  7. extractionthe mixture was extracted three times with ethyl acetate
  8. washThe combined extracts were washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-9c188e9f828645758836b8d617beb312
Source dataset
uspto-grants-1990_01
Patent number
US04891363

Reaction notes

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