1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Methoxy-3-(4-methoxyphenyl)benzylazide

HRID 460137Notes

Reaction equation

HRID 460137 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]O)=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1.C1(P([N:33]=[N+:34]=[N-:35])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1COCC1>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][N:33]=[N+:34]=[N-:35])=[CH:5][C:4]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azide2×HCID 688416394-Methoxy-3-(4-methoxyphenyl)benzyl alcohol

Product 1

HCID 223912444-Methoxy-3-(4-methoxyphenyl)benzylazideYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-methoxy-3-(4-methoxyphenyl)benzyl alcohol (0.88 g, 3.59 mmol) and diphenylphosphoryl azide (1.18 g, 4.32 mmol) in anhydrous THF (15 mL) was cooled in an ice-bath prior to addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (0.87 g, 5.76 mmol). The resulting mixture was then stirred at room temperature for 48 hours. More diphenylphosphoryl azide was added (1.4 mol, 0.39 g) and the mixture stirred for further 16 hours. The solvent was then evaporated, the residue taken into dichloromethane and washed with acid. The organic layer was separated and the solvent removed under reduced pressure to afford 0.82 g of title compound.

Workup

  1. stirringthe mixture stirred for further 16 hours
  2. customThe solvent was then evaporated
  3. washwashed with acid
  4. customThe organic layer was separated
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-470651a610f043b39c26d3992136d19d
Source dataset
uspto-grants-2007_03
Patent number
US07196102B2

Reaction notes

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