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

HRID 845816Notes

Reaction equation

HRID 845816 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-7e251f6cddd847e39e92765ded062cd3
Source dataset
uspto-grants-1988_07
Patent number
US04760086

Reaction notes

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