Sodium Azide → 2-Azido-1,1-diphenylpropanol

HRID 974202Notes

Reaction equation

HRID 974202 reaction equation
[C:1]1([C:7]2([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:9]([CH3:10])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C)C=O.O>[N:17]([CH:9]([CH3:10])[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[OH:8])=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 110958912,2-Diphenyl-3-methyloxirane

Product 1

HCID 150100222-Azido-1,1-diphenylpropanolYield 70%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

A solution of 9.35 g (44.5 mmol) 2,2-diphenyl-3-methyloxirane and 9.00 g (138 mmol) NaN3 in 100 ml of 2:1 N,N-dimethylformamide-water was heated at reflux for 72 hours. The solution was concentrated and the residue was partitioned between ether and water. The ether layer was washed with NaHCO3, then water, dried over Na2SO4 and concentrated. HPLC (5% EtOAc-hexane) afforded 7.86 g (70%) of 2-azido-1,1-diphenylpropanol as a clean oil.

Workup

  1. temperatureat reflux for 72 hours
  2. concentrationThe solution was concentrated
  3. customthe residue was partitioned between ether and water
  4. washThe ether layer was washed with NaHCO3
  5. dry with materialwater, dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec5743d28da24c2d97d957c9eb0db650
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

Loading…