Sodium Azide → 3-(2-Azidoethyl)-2,2-dimethyl-chroman

HRID 1196049Notes

Reaction equation

HRID 1196049 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]1([CH3:29])[CH:15]([CH2:16][CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7]1>O.C(O)C>[N:1]([CH2:17][CH2:16][CH:15]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[O:7][C:6]1([CH3:5])[CH3:29])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 540378412,2-Dimethyl-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

Product 1

HCID 538675953-(2-Azidoethyl)-2,2-dimethyl-chroman

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3.9 g (60 mmol) of sodium azide in 10 ml of water is added to a solution of 14.4 g (40 mmol) of 2,2-dimethyl-3-[2-(4-toluenesulfonyloxy)-ethyl]-chroman (prepared as described in Example 38) in 200 ml of ethanol. The mixture is boiled under reflux for 18 hours. After cooling, the ethanol is evaporated off in vacuo, water is added to the residue and extraction is carried out with dichloromethane. The dichloromethane phase is washed with water, dried over sodium sulfate and concentrated by evaporation, yielding 8.7 g (94% of the theoretical yield) of 3-(2-azidoethyl)-2,2-dimethyl-chroman in the form of a yellow oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. customthe ethanol is evaporated off in vacuo, water
  4. additionis added to the residue and extraction
  5. washThe dichloromethane phase is washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customyielding 8.7 g (94% of the

Sources & evidence

ORD record
ord-335664877a9142b1898c3d69cb6b9b13
Source dataset
uspto-grants-1992_05
Patent number
US05112855

Reaction notes

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