Triphenylphosphine → 5-(1-Azido-2-ethylbutyl)-1-(benzyloxy)-1H-pyrazole

HRID 748075Notes

Reaction equation

HRID 748075 reaction equation
[CH2:1]([O:8][N:9]1[C:13]([CH:14](O)[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][CH:11]=[N:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:66]=[N+:67]=[N-:68])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:66]([CH:14]([C:13]1[N:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:10]=[CH:11][CH:12]=1)[CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[N+:67]=[N-:68]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 685933741-[1-(Benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutan-1-ol

Product 1

HCID 866000085-(1-Azido-2-ethylbutyl)-1-(benzyloxy)-1H-pyrazoleYield 67.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 1-[1-(benzyloxy)-1H-pyrazol-5-yl]-2-ethylbutan-1-ol (0.492 g, 1.79 mmol) in THF (17 mL) at 0° C. under a nitrogen atmosphere was added triphenyl phosphine (0.705 g, 2.69 mmol) followed by diethyl azodicarboxylate (0.42 mL, 2.7 mmol). Diphenyl phosphoryl azide (0.58 mL, 2.7 mmol) was then added over 4 min. The mixture was allowed to attain ambient temperature and stirred for 16 h. The solvent was then evaporated in vacuo producing a crude oil which was purified on a Biotage column (hexane/ethyl acetate, 9:1). This afforded the product as a clear colorless oil (0.36 g, 67%). Mass Spectrum (+ESI): 300 (M+H)+.

Workup

  1. customto attain ambient temperature
  2. customThe solvent was then evaporated in vacuo
  3. customproducing a crude oil which
  4. customwas purified on a Biotage column (hexane/ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-340f8ebbb9db438f82975011bd07a093
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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