Ethyl cyanoacetate → HCID 20251327, compound

HRID 1285018Notes

Reaction equation

HRID 1285018 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].I[CH2:12][CH2:13][O:14][CH:15]([O:17][CH2:18][CH2:19]I)[CH3:16]>O1CCCC1>[C:3]([CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:12][CH2:13][O:14][CH:15]([O:17][CH2:18][CH2:19][CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:3]#[N:4])[CH3:16])#[N:4]

Participants

5

Reactant 3

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

Product 1

HCID 20251327HCID 20251327, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5.28 g (0.11 mol) of sodium hydride was added to 50 ml of dry tetrahydrofuran, and to this solution was added dropwise a mixed solution of 12.2 g (0.11 mol) of ethyl cyanoacetate and 10.0 g (0.027 mol) of bis(2-iodoethoxy)ethane, followed by 2-hours reflux under heating. After the reaction, the most portion of tetrahydrofuran was distilled off and the residue was added with 10 ml of water, neutralized with 1N hydrochloric acid and extracted three times with 50 ml of ether. After drying the extract over anhydrous sodium sulfate, ether was distilled off and the resultant oily product was passed through a basic alumina (activity II)-packed column and eluted with petroleum ether-ether (1:4) to obtain 5.14 g of bis(3-cyano-3-carboethoxypropoxy)ethane, ##STR32## (yield: 56%). The property analyses of this compound gave the following results.

Workup

  1. waitfollowed by 2-hours
  2. temperaturereflux
  3. temperatureunder heating
  4. customAfter the reaction
  5. distillationthe most portion of tetrahydrofuran was distilled off
  6. additionthe residue was added with 10 ml of water
  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 (1:4)

Sources & evidence

ORD record
ord-b3e9f33836ee40f4a0c472856c02787a
Source dataset
uspto-grants-1986_01
Patent number
US04564690

Reaction notes

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