Triphenylphosphine → 1-Azido-3-(3-methoxyphenyl)-1-phenylpropane

HRID 278162Notes

Reaction equation

HRID 278162 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[CH:6]=[CH:7][CH:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:64]([CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)=[N+:65]=[N-:66]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 142247333-(3-Methoxypheny)-1-phenylpropanol

Product 1

HCID 226271071-Azido-3-(3-methoxyphenyl)-1-phenylpropane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step A (1.36 g, 5.6 mmol) in 20 mL of THF at 0° C. under Ar was added triphenylphosphine (1.8 g, 6.9 mmol), diethylazodicarboxylate (1.12 mL, 6.9 mmol) and diphenylphosphoryl azide (1.52 mL, 6.9 mmol). The ice-bath was removed and the reaction mixture was stirred at ambient temperature for 20 hours. The reaction was concentrated in vacuo and purified by silica gel chromatography (2% EtOAc/Hexane) to provide the desired product as a nearly colorless gum.

Workup

  1. customThe ice-bath was removed
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified by silica gel chromatography (2% EtOAc/Hexane)

Sources & evidence

ORD record
ord-9f0ee46862304d42b877f01e29ccae2d
Source dataset
uspto-grants-2002_03
Patent number
US06358985B1

Reaction notes

Loading…