Diethyl Malonate → 667871-49-0

HRID 1098092Notes

Reaction equation

HRID 1098092 reaction equation
[Na].[C:2]([O:10][CH2:11][CH3:12])(=[O:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20]>CCO>[CH2:11]([O:10][C:2](=[O:9])[CH:3]([CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH3:20])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:12]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 1235321-Bromo-3,6-dioxaheptaneHCID 5360545Sodium2×

Product 1

HCID 58583956667871-49-0Yield 48.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.72 g, 31.31 mmol) was added in portions to EtOH (99.5%, 35 mL) under stirring. When all sodium had dissolved, diethyl malonate (4.80 g, 29.97 mmol) was added slowly during 5 minutes and the reaction mixture was stirred for another 15 minutes. 1-Bromo-2-(2-methoxyethoxy)-ethane (5.50 g, 30.05 mmol) was added and the reaction mixture was refluxed for 2 hrs. Any solids were filtered off and the clear solution was concentrated in vacuo. The residue was taken up in water and diethyl ether and the two phases were separated. The organic phase was dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1) to give the title compound as a colourless oil (3.80 g), 1H NMR (300 MHz, CDCl3) δ 4.19 (q, 4H), 3.54 (m, 7H), 3.38 (s, 3H), 2.19 (m, 2H), 1.27 (t, 6H).

Workup

  1. stirringthe reaction mixture was stirred for another 15 minutes
  2. temperaturethe reaction mixture was refluxed for 2 hrs
  3. filtrationAny solids were filtered off
  4. concentrationthe clear solution was concentrated in vacuo
  5. customdiethyl ether and the two phases were separated
  6. dry with materialThe organic phase was dried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified with column chromatography (silica gel, eluting with EtOAc/MeOH:20/1)

Sources & evidence

ORD record
ord-3e938d6a8f7f4b01b2106251971c288f
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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