Triphenylphosphine → HCID 10512677, compound

HRID 1954231Notes

Reaction equation

HRID 1954231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH2:13][CH2:14][N:15]=[N+]=[N-])[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][CH2:13][CH2:14][NH2:15])[CH:11]=1)[O:8][CH2:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 11817232HCID 11817232, compound

Product 1

HCID 10512677HCID 10512677, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(6-fluorochroman-8-yloxy)ethylazide (4.12 g, 0.017 mol) and triphenylphosphine (6.83 g, 0.026 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 (40% methanol-methylene chloride plus ammonium hydroxide) afforded 3.45 g (94%) of product as a white solid: mp 68-70° C.

Workup

  1. customThe solvent was removed under vacuum
  2. customChromatography (ethyl acetate) removed triphenylphosphine and triphenylphosphine oxide and (40% methanol-methylene chloride plus ammonium hydroxide)

Sources & evidence

ORD record
ord-3629c12e48b4418eb8cd2cda9662f5ee
Source dataset
uspto-grants-2000_09
Patent number
US06121307

Reaction notes

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