Triphenylphosphine → HCID 11159719, compound

HRID 1954224Notes

Reaction equation

HRID 1954224 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=1)[O:7][CH2:8][CH2:9][N:10]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=1)[O:7][CH2:8][CH2:9][NH2:10]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 11310359HCID 11310359, compound

Product 1

HCID 11159719HCID 11159719, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(5-fluoro-2-methoxy-phenoxy)ethylazide (3.97 g, 0.019 mol) and triphenylphosphine (5.95 g, 0.023 mol) in tetrahydrofuran (80 ml) and water (1.5 ml) was allowed to stir for 18 hours at room temperature. The solvent was removed under vacuum. Chromatography (ethyl acetate) removed triphenylphosphine and triphenylphosphine oxide and (25-50% methanol-ethyl acetate plus ammonium hydroxide) afforded 3.14 g (90%) of product as a clear oil. MS EI m/e 185 (M+).

Workup

  1. customThe solvent was removed under vacuum
  2. customChromatography (ethyl acetate) removed triphenylphosphine and triphenylphosphine oxide and (25-50% methanol-ethyl acetate plus ammonium hydroxide)

Sources & evidence

ORD record
ord-9aaa59c6dbb048cab7621f8d96aa5fcc
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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