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Triphenylphosphine → 5-(1-azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazole

HRID 748037
Notes
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Reaction equation

HRID 748037 reaction equation
[CH2:1]([CH:3]([CH2:20][CH3:21])[CH:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:9]=[CH:8][CH:7]=1)O)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(P([N:67]=[N+:68]=[N-:69])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[N:67]([CH:4]([C:6]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[N:9]=[CH:8][CH:7]=1)[CH:3]([CH2:20][CH3:21])[CH2:1][CH3:2])=[N+:68]=[N-:69]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 685942442-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol

Product 1

HCID 866000025-(1-azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazoleYield 66%

Reagents, catalysts & solvents

1
HCID 8028TetrahydrofuranSolvent

Procedure

To 2-ethyl-1-[1-(4-methoxybenzyl)-1H-pyrazol-5-yl]butan-1-ol (1.21 g, 4.20 mmol) in THF (40 mL) at 0° C. was added triphenylphosphine (1.65 g, 6.29 mmol), diethyl azodicarboxylate (1.0 mL, 6.3 mmol), and diphenylphosphoryl azide (1.4 mL, 6.3 mmol). The reaction mixture was warmed to room temperature and stirred for 15.5 h. The solvent was removed in vacuo and the resulting residue was purified by column chromatography (EtOAc/hexanes, 1:9, then 1:4) to give 0.862 g (66%) of 5-(1-azido-2-ethylbutyl)-1-(4-methoxybenzyl)-1H-pyrazole.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe resulting residue was purified by column chromatography (EtOAc/hexanes, 1:9

Sources & evidence

ORD record
ord-714ab6c9e59842a1a33fc706345acb58
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07399778B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes