Diethyl Malonate → Diethyl [3-(3-pyridyl)-propyl]malonate

HRID 1494062Notes

Reaction equation

HRID 1494062 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Na].Br.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH2:22]Br)[CH:15]=1>C(O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][CH2:21][CH2:22][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])[CH:15]=1

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 127015693-(3-Bromopropyl)pyridine hydrobromide

Product 1

HCID 10468827Diethyl [3-(3-pyridyl)-propyl]malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 48 mL (0.37 mole) of diethyl malonate in 960 mL ethanol is added 14.03 g (0.61 mole) sodium metal and the mixture is stirred until all of the metal dissolved. The solution is heated to reflux and a solution of 80.04 g (0.28 mole) of 3-(3-pyridyl)-propyl bromide hydrobromide in 960 mL ethanol is added rapidly and the mixture is maintained at reflux for 10 hours. The reaction mixture is evaporated and the residue is taken up in 400 mL of 1N aqueous hydrochloric acid and washed with 400 mL hexane. The aqueous phase is adjusted to pH 8 using solid sodium bicarbonate. The mixture is then extracted with methylene chloride (3×200 mL). Combined organic extracts are dried (MgSO4), filtered and evaporated to dryness to give diethyl [3-(3-pyridyl)-propyl]-malonate as an oil.

Workup

  1. dissolutiondissolved
  2. temperatureThe solution is heated
  3. temperatureto reflux
  4. temperaturethe mixture is maintained
  5. temperatureat reflux for 10 hours
  6. customThe reaction mixture is evaporated
  7. washwashed with 400 mL hexane
  8. extractionThe mixture is then extracted with methylene chloride (3×200 mL)
  9. dry with materialCombined organic extracts are dried (MgSO4)
  10. filtrationfiltered
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-d679882bf6634677a11492f3bc56fc09
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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