Butanenitrile, 4,4′-[oxybis(2,1-ethanediyloxy)]bis- → HCID 22572558, compound

HRID 433853Notes

Reaction equation

HRID 433853 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])#[N:2]>C1COCC1>[NH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][CH2:3][CH2:1][NH2:2]

Participants

3

Reactant 1

HCID 22572554Butanenitrile, 4,4′-[oxybis(2,1-ethanediyloxy)]bis-

Product 1

HCID 22572558HCID 22572558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of 50 mL dry THF containing 0.42 g (10.4 mmol) fresh LAH was heated to gentle reflux under argon for 15 minutes. 0.5 g (2 mmol) 17 in 15 mL dry THF was added dropwise over 20 minutes, maintaining a gentle reflux. The unreacted LAH was quenched with ethanol, and the mixture was treated with dropwise addition of saturated sodium sulfate under efficient stirring until a white precipitate formed. The mixture was filtered, and the precipitate was washed 6×30 mL with THF. The organic extracts were combined and the solvent was removed by rotary evaporation to yield an oil. ESI-MS: predicted, 248.1; observed, 249.1 (M+H+)+

Workup

  1. temperatureto gentle reflux under argon for 15 minutes
  2. temperaturemaintaining a gentle reflux
  3. customThe unreacted LAH was quenched with ethanol
  4. additionthe mixture was treated with dropwise addition of saturated sodium sulfate
  5. customformed
  6. filtrationThe mixture was filtered
  7. washthe precipitate was washed 6×30 mL with THF
  8. customthe solvent was removed by rotary evaporation
  9. customto yield an oil

Sources & evidence

ORD record
ord-c263b4e9079f430e8105cf289a9f27f5
Source dataset
uspto-grants-2003_12
Patent number
US06670194B1

Reaction notes

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