1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 42625428, compound

HRID 2236662Notes

Reaction equation

HRID 2236662 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:17](O)[CH3:18])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1>[N:34]([CH:17]([C:11]1[CH:12]=[CH:13][C:14]([O:15][CH3:16])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:10]=1)[CH3:18])=[N+:35]=[N-:36]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 42625427HCID 42625427, compound

Product 1

HCID 42625428HCID 42625428, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of crude 1-(3-benzyloxy-4-methoxy-phenyl)-ethanol (10 mmol maximum) and diphenylphosphoryl azide (2.6 mL, 12 mmol) in toluene (18 mL) is added 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU, 1.6 mL, 11 mmol). The mixture is stirred at 0° C. for two hours and then at room temperature overnight. The reaction mixture is washed with water and concentrated to give 4-(1-azido-ethyl)-2-benzyloxy-1-methoxybenzene, which is used in the next step without purification.

Workup

  1. customat room temperature
  2. customovernight
  3. washThe reaction mixture is washed with water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-59682e59ef8b479392ec1c1b741273ee
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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