1,8-Diazabicyclo(5.4.0)undec-7-ene → 2-Allyloxy-5-methoxybenzyl azide

HRID 501729Notes

Reaction equation

HRID 501729 reaction equation
[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:6]=1[CH2:7]O)[CH:2]=[CH2:3].C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1COCC1>[CH2:1]([O:4][C:5]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:6]=1[CH2:7][N:29]=[N+:30]=[N-:31])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 432678902-Allyloxy-5-methoxybenzyl alcohol

Product 1

HCID 866223532-Allyloxy-5-methoxybenzyl azideYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step AS (3). To a solution of 2-allyloxy-5-methoxybenzyl alcohol (5 g, 26 mmol) in 75 mL of anhydrous THF was added diphenylphosphoryl azide (6 mL, 28.5 mmol) and 1,8-diazabicyclo[5,4,0]undec-7-ene (DBU) (4.6 mL, 31 mmol) at 0° C. The mixture was refluxed for 1 h. The reaction was concentrated and the residue purified by silica gel chromatography eluting with 25% EtOAc in hexane to yield 2-allyloxy-5-methoxybenzyl azide as a colorless oil (4.9 g, 87%). (M−N3)+=177; 1H NMR (400 MHz, CDCl3) δ ppm 3.76 (s, 3H) 4.36 (s, 2H) 4.47-4.57 (m, 2H) 5.21-5.31 (m, 1H) 5.31-5.46 (m, 1H) 5.95-6.14 (m, 1H) 6.79-6.82 (m, 2H) 6.83-6.85 (m, 1H).

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. concentrationThe reaction was concentrated
  3. customthe residue purified by silica gel chromatography
  4. washeluting with 25% EtOAc in hexane

Sources & evidence

ORD record
ord-b4d9fc5a0041485ca8d5ce3eec47045e
Source dataset
uspto-grants-2010_08
Patent number
US07772221B2

Reaction notes

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