Triphenylphosphine → HCID 18357641, compound

HRID 428033Notes

Reaction equation

HRID 428033 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH:16]([CH2:18][CH:19]=[CH2:20])O)=[N:2]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>C1C=CC=CC=1>[N:66]([CH:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[O:1][N:2]=1)[CH2:18][C:19]#[CH:20])=[N+:67]=[N-:68]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 18357579HCID 18357579, compound

Product 1

HCID 18357641HCID 18357641, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture containing 4.0 g of 2-(1,2-benzisoxazol-3-yl)-α-2-propenyl-benzenemethanol, 4.32 g of triphenylphosphine, 2.61 g of diethyl azodicarboxylate and 4.12 g of diphenylphosphoryl azide in 50 ml of benzene was stirred at room temperature for 24 h. Evaporation of the solvent under reduced pressure afforded a solid which was purified by chromatography on silica gel, eluting with 5% ethanol in toluene, to afford 1.5 g of 3-[2-(1-azido-3-butynyl)phenyl]-1,2-benzisoxazole as an oil, M.S. (C.I:)-(M/Z): 289 [M+H]+.

Workup

  1. customEvaporation of the solvent under reduced pressure
  2. customafforded a solid which
  3. customwas purified by chromatography on silica gel
  4. washeluting with 5% ethanol in toluene

Sources & evidence

ORD record
ord-d66b333179c741b5b64d6330a5d5bb57
Source dataset
uspto-grants-2001_11
Patent number
US06313139B1

Reaction notes

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