Triphenylphosphine → HCID 15550301, compound

HRID 1422142Notes

Reaction equation

HRID 1422142 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:18]=[CH:17][CH:16]=[CH:15][C:11]=2[CH:12](O)[CH3:13])=[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:64]=[N+:65]=[N-:66])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:64]([CH:12]([C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][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)[CH3:13])=[N+:65]=[N-:66]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 15550300HCID 15550300, compound

Product 1

HCID 15550301HCID 15550301, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 0.6 g of 2-[2-(1,2-benzisoxazol-3-yl]-a-methylbenzyl alcohol and 0.65 g of triphenylphosphine in 10 ml tetrahydrofuran at 0° C. was added 0.39 ml of diethyl azodicarboxylate followed by a solution of 0.54 ml of diphenylphosphoryl azide in 5 ml of tetrahydrofuran. The solution was warmed to room temperature and stirred for 1.5 h. The reaction was evaporated and purified by flash chromatography eluting with 1:1 toluene-heptane to yield 0.27 g of 3-[2-(1-azidoethyl)-phenyl]-1,2-benzisoxazole as a colourless gum, 1H-NMR (200 MHz, CDCl3) dH 5.10 (CHN3).

Workup

  1. customThe reaction was evaporated
  2. custompurified by flash chromatography
  3. washeluting with 1:1 toluene-heptane

Sources & evidence

ORD record
ord-e9070aa9ce7f47bfaff56d1da199356f
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

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