Diboron → 2-{4-[(Butan-2-yl)oxy]phenoxy}ethan-1-amine

HRID 1073437Notes

Reaction equation

HRID 1073437 reaction equation
[CH3:1][CH:2]([O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][C:12]#[N:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4].B#B>C1COCC1>[CH3:1][CH:2]([O:5][C:6]1[CH:15]=[CH:14][C:9]([O:10][CH2:11][CH2:12][NH2:13])=[CH:8][CH:7]=1)[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6328200DiboronHCID 156625734-(1-Methylpropoxy)phenoxyacetonitrile

Product 1

HCID 142781892-{4-[(Butan-2-yl)oxy]phenoxy}ethan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the above phenoxyacetonitrile (7.21 g, 35.2 mmol) in 60 ml of THF at 8° is added 1M diborane (61.50 g, 61.5 mmol) over 45 min. The reaction is warmed to RT and stirred for 6 hours. The reaction is stirred for 16 hours. The THF-H2O is removed in vacuo and water and ether are added to the white solid, followed by 10% aqueous sodium hydroxide to basify. The product is extracted with ether (3×) and the combined organic phases are washed with water and with brine, dried, filtered and solvent removed to give 2-[4-(1-methylpropoxy)phenoxy]ethylamine.

Workup

  1. stirringThe reaction is stirred for 16 hours
  2. customThe THF-H2O is removed in vacuo and water and ether
  3. additionare added to the white solid
  4. extractionThe product is extracted with ether (3×)
  5. washthe combined organic phases are washed with water and with brine
  6. customdried
  7. filtrationfiltered
  8. customsolvent removed

Sources & evidence

ORD record
ord-bf710438837b4e1fa3918ba521c5b2e5
Source dataset
uspto-grants-1990_11
Patent number
US04968829

Reaction notes

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