Water → HCID 18687685, compound

HRID 1872850Notes

Reaction equation

HRID 1872850 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:4]=1[O:5][CH2:6][CH2:7][N:8]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:4]=1[O:5][CH2:6][CH2:7][NH2:8]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 18687670HCID 18687670, compound

Product 1

HCID 18687685HCID 18687685, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(2-methoxy-4,5-difluoro-phenoxy)-ethylazide (0.69 g, 3.46 mmol) and triphenylphosphine (1.27 g, 4.84 mmol) in tetrahydrofuran (15 ml) containing water (0.08 ml) was stirred at room temperature overnight. The solvent was removed under vacuum. Chromatography with ethyl acetate removed triphenylphosphine oxide, followed elution with ethyl acetate-methanol-ammonium hydroxide 8.5:1.5:0.5, afforded 0.53 g of product as a white solid: mp 44-46° C.; MS EI m/e 203 (M+).

Workup

  1. customThe solvent was removed under vacuum
  2. customChromatography with ethyl acetate removed triphenylphosphine oxide
  3. washelution with ethyl acetate-methanol-ammonium hydroxide 8.5:1.5:0.5

Sources & evidence

ORD record
ord-ce946116bb0a4c468dec2bc12a183387
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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