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

HRID 2248190Notes

Reaction equation

HRID 2248190 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 while sold, followed by 10% aqueous sodium hydroxide to basify. The product is extracted with ether (3X) 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 while
  4. extractionThe product is extracted with ether (3X)
  5. washthe combined organic phases are washed with water and with brine
  6. customdried
  7. filtrationfiltered
  8. customsolvent removed

Sources & evidence

ORD record
ord-ca84135a0f454bf6a28722a92fe32f46
Source dataset
uspto-grants-1991_08
Patent number
US05037991

Reaction notes

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