1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18373575, compound

HRID 2301488Notes

Reaction equation

HRID 2301488 reaction equation
[CH3:1][CH:2](O)[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.C1(P([N:25]=[N+:26]=[N-:27])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:25]([CH:2]([C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1)[CH3:1])=[N+:26]=[N-:27]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 953521-(4-Bromophenyl)ethanolHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 18373575HCID 18373575, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 10.0 g (49.7 mmol) of 4-bromo-a-methylbenzyl alcohol and 16.4 g (59.6 mmol) of diphenylphosphoryl azide in 70 mL of toluene was added 9.1 g of 1,8-diazabicyclo[5.4.0]undec-7-ene and the mixture was stirred at room temperature for 16 hours. The reaction mixture was washed once with 30 mL of 10% aqueous sodium bisulfate. The organic layer was separated and the aqueous layer was extracted three times with 10 mL each of ethyl acetate. The combined organics were dried (MgSO4), filtered and concentrated in vacuo to afford 11.2 g (100%) of the title compound.

Workup

  1. washThe reaction mixture was washed once with 30 mL of 10% aqueous sodium bisulfate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with 10 mL each of ethyl acetate
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1bf0fb3c029f4a5aa757f2b65ab19a08
Source dataset
uspto-grants-2002_12
Patent number
US06500865B1

Reaction notes

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