Ethyl cyanoacetate → HCID 13668627, compound

HRID 1285019Notes

Reaction equation

HRID 1285019 reaction equation
[H-].[Na+].ICCO[CH:7]([O:9][CH2:10][CH2:11][I:12])[CH3:8].[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14]>O1CCCC1>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:13]#[N:14])([CH2:20][CH2:19][O:18][CH2:8][CH2:7][O:9][CH2:10][CH2:11][I:12])[CH2:15][CH2:16][O:17][CH2:8][CH2:7][O:9][CH2:10][CH2:11][I:12])[CH3:20]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 18403935HCID 18403935, compound

Product 1

HCID 13668627HCID 13668627, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.71 g (0.036 mol) of sodium hydride was added to 40 ml of tetrahydrofuran dried with 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 1.35 g (0.012 mol) of ethyl cyanoacetate, followed by 5-hours reflux under heating. Tetrahydrofuran was distilled off and the residue was cooled to room temperature, added with 1N hydrochloric acid until the litmus paper came to show 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 basic alumina (activity II)-packed column and eluted with petroleum ether-ether (2:1) to obtain 3.43 g of 2,2-bis(8-iodo-3,6-dioxaoctyl)cyanoacetic acid ethyl ester, ##STR33## (yield: 48%).

Workup

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

Sources & evidence

ORD record
ord-0cb8bdcccef94d4089a39dc66b3b4e08
Source dataset
uspto-grants-1986_01
Patent number
US04564690

Reaction notes

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