Diethyl Malonate → HCID 13668629, compound

HRID 1285023Notes

Reaction equation

HRID 1285023 reaction equation
[H-].[Na+].ICCO[CH:7]([O:9][CH2:10][CH2:11][I:12])[CH3:8].[C:13]([O:21][CH2:22][CH3:23])(=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>O1CCCC1>[CH2:22]([O:21][C:13](=[O:20])[C:14]([CH2:19][CH2:18][O:17][CH2:8][CH2:7][O:9][CH2:10][CH2:11][I:12])([CH2:14][CH2:15][O:16][CH2:8][CH2:7][O:9][CH2:10][CH2:11][I:12])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH3:23]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 18403935HCID 18403935, compound

Product 1

HCID 13668629HCID 13668629, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.71 g (0.036 mol) of sodium hydride was added to 40 ml of tetrahydrofuran dried over metallic sodium, and to this solution was added dropwise a mixed solution of 17.6 g (0.048 mol) of bis(2-iodoethoxy)ethane and 1.92 g (0.012 mol) of diethyl malonate, the mixture being refluxed under heating for hours. Tetrahydrofuran was distilled off and the residue was cooled to room temperature, added with 1N hydrochloric acid until the litmus paper came to indicate acidity and then extracted three times with 50 ml of ether. After drying the extract over anhydrous sodium sulfate, ether was distilled off and the oily residue was passed through a silica gel-packed column and eluted with petroleum ether-ether (2:1) to obtain 2.90 g of 2,2-bis(8-iodo-3,6-dioxaoctyl)malonic acid diethyl ester, (ICH2CH2OCH2CH2OCH2CH2)2 -C(CO2Et)2 (yield: 38%).

Workup

  1. dry with materialdried over metallic sodium
  2. temperaturethe mixture being refluxed
  3. temperatureunder heating for hours
  4. distillationTetrahydrofuran was distilled off
  5. additionadded with 1N hydrochloric acid until the litmus paper
  6. extractionextracted three times with 50 ml of ether
  7. customAfter drying the
  8. extractionextract over anhydrous sodium sulfate, ether
  9. distillationwas distilled off
  10. washeluted with petroleum ether-ether (2:1)

Sources & evidence

ORD record
ord-9dcbcca507ea46ffba05f2c3571cbbe7
Source dataset
uspto-grants-1986_01
Patent number
US04564690

Reaction notes

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