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

HRID 2113115Notes

Reaction equation

HRID 2113115 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-b1ff11a4f0ad4aafbb0efa37128069d0
Source dataset
uspto-grants-2009_04
Patent number
US07524873B2

Reaction notes

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