Triphenylphosphine → HCID 22929954, compound

HRID 1296007Notes

Reaction equation

HRID 1296007 reaction equation
[N:1]([CH2:4][C:5]1[C:6]([C:13]#[N:14])=[N:7][C:8]([CH2:11][CH3:12])=[CH:9][CH:10]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[CH2:11]([C:8]1[N:7]=[C:6]2[C:13]([NH2:14])=[N:1][CH2:4][C:5]2=[CH:10][CH:9]=1)[CH3:12]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 22929930HCID 22929930, compound

Product 1

HCID 22929954HCID 22929954, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 3-(azidomethyl)-6-ethyl-2-pyridinecarbonitrile (1.0 g, 5.34 mmol) in tetrahydrofuran (16 ml)-water (0.8 ml), triphenylphosphine (2.1 g, 8.01 mmol) was added while stirring on ice, and the mixture was further stirred at room temperature for 2.0 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (solvent: ethyl acetate, ethyl acetate:methanol=4:1, ethyl acetate:methanol:aqueous ammonia=2:1:0.1 in this order). The title compound (0.769 g) was obtained as a light green substance. (89.3% yield)

Workup

  1. additionwas added
  2. stirringthe mixture was further stirred at room temperature for 2.0 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (solvent

Sources & evidence

ORD record
ord-6f52400b20914dd688b8b850b1f738a9
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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