Triphenylphosphine → HCID 86591651, compound

HRID 985567Notes

Reaction equation

HRID 985567 reaction equation
[C:1]([O:7][CH2:8][CH:9]([CH2:20]O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].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>[C:1]([O:7][CH2:8][CH:9]([CH2:20][N:67]=[N+:68]=[N-:69])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=1)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 22507352HCID 22507352, compound

Product 1

HCID 86591651HCID 86591651, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of alcohol (17) (10 mmol), triphenylphospine (20 mmol, 5.25 g), diethyl azodicarboxylate (20 mmol, 3.15 ml) in THF (70 ml) was treated with diphenylphosphorylazide (20 mmol, 4.32 ml) and stirred at room temperature for 18 h. The solvent was removed in vacuo and the residue was purified by column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant to give compound 19.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography on silica gel with EtOAc/hexanes (1:10) as an eluant

Sources & evidence

ORD record
ord-3600ab64068a49f6bd953fe33606f640
Source dataset
uspto-grants-2005_03
Patent number
US06872748B2

Reaction notes

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