Triphenylphosphine → HCID 11159719, compound

HRID 1872837Notes

Reaction equation

HRID 1872837 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 followed by 25-50% methanol-ethyl acetate plus ammonium hydroxide) removed triphenylphosphine and triphenylphosphine oxide and 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 followed by 25-50% methanol-ethyl acetate plus ammonium hydroxide) removed triphenylphosphine and triphenylphosphine oxide

Sources & evidence

ORD record
ord-c6ee09ff6a2241d0873acdec5eca7905
Source dataset
uspto-grants-2000_08
Patent number
US06110956

Reaction notes

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