Triphenylphosphine → 5-(3-Nitro-phenoxy)-pentylamine

HRID 599180Notes

Reaction equation

HRID 599180 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[CH:11]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O>[N+:16]([C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][CH:13]=1)[O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][NH2:1])([O-:18])=[O:17]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 866252691-(5-Azido-pentyloxy)-3-nitro-benzene

Product 1

HCID 690096135-(3-Nitro-phenoxy)-pentylamineYield 98.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(5-azido-pentyloxy)-3-nitro-benzene (3.12 g, 12.5 mmol) in 50 mL THF and 1 mL H2O was added triphenylphosphine (3.27 g, 12.5 mmol). The reaction mixture was stirred at room temperature for 48 hours and then was partitioned with ethyl acetate and water. The aqueous solution was extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with brine, dried over MgSO4, and concentrated to give a yellow liquid, which was purified by silica gel column chromatography to give 5-(3-nitro-phenoxy)-pentylamine (2.75 g, 12.3 mmol, 98%) as a yellow liquid.

Workup

  1. customwas partitioned with ethyl acetate and water
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×50 mL)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a yellow liquid, which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9f82ef0b39a24dd39826c94ce0c8547c
Source dataset
uspto-grants-2011_03
Patent number
US07897764B2

Reaction notes

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