Triphenylphosphine → HCID 21875609, compound

HRID 967848Notes

Reaction equation

HRID 967848 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15]O)=[CH:10][CH:9]=2)[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[N:4]=1)[CH3:2].N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P([N:66]=[N+:67]=[N-:68])(C2C=CC=CC=2)=O)C=CC=CC=1>>[CH2:1]([C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N:66]=[N+:67]=[N-:68])=[CH:10][CH:9]=2)[C:6]2[CH:17]=[CH:18][CH:19]=[CH:20][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 21876352HCID 21876352, compound

Product 1

HCID 21875609HCID 21875609, compoundYield 100.9%

Procedure

A mixture of 2-[4-(2-ethyl-1H-benzimidazol-1-yl)phenyl]ethanol (914 mg, 3.4 mmol) in TUF (40 mL) was added diethyl azodicarboxylate (DEAD) (1.2 mg, 7 mmol), triphenylphosphine (1.8 g, 7 mmol) and diphenylphosphoryl azide (DPPA) (1.9 g, 7 mmol). The mixture was stirred at room temperature for 4.5 h. After removal of solvent, the residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2) to afford 1000 mg (74%) of the title compound as a brown oil: MS (EI) m/z 291 (M+)

Workup

  1. customAfter removal of solvent
  2. customthe residue was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (gradient elution from 1:1 to 1:2)

Sources & evidence

ORD record
ord-167e0888e24e4d778e43a7b8db678aa9
Source dataset
uspto-grants-2005_10
Patent number
US06956050B2

Reaction notes

Loading…