Sodium Azide → 3-(2-Azidoethyl)-2,2-dimethyl-6-fluorochroman

HRID 1032439Notes

Reaction equation

HRID 1032439 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][C:6]1([CH3:30])[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]=[C:11]([F:29])[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]=[C:11]([F:29])[CH:12]=2)[O:7][C:6]1([CH3:5])[CH3:30])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 543823572,2-Dimethyl-6-fluoro-3-[2-(4-toluenesulfonyloxy)ethyl]-chroman

Product 1

HCID 543835353-(2-Azidoethyl)-2,2-dimethyl-6-fluorochroman

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1.62 g (24.9 mmol) of sodium azide in 10 ml of water is added to a solution of 6.3 g (16.6 mmol) of 2,2-dimethyl-6-fluoro-3-[2-(4-toluenesulfonyloxy)-ethyl]-chroman in 100 ml of ethanol. The mixture is boiled under reflux for 18 hours. After cooling, the ethanol is evaporated off in vacuo and water is added to the residue. The aqueous mixture is extracted with diethyl ether. The combined organic phases are washed with water, dried over sodium sulfate and concentrated by evaporation in vacuo, yielding 4.13 g (100% of the theoretical yield) of 3-(2-azidoethyl)-2,2-dimethyl-6-fluoro-chroman in the form of a light-yellow oil.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. customthe ethanol is evaporated off in vacuo and water
  4. additionis added to the residue
  5. extractionThe aqueous mixture is extracted with diethyl ether
  6. washThe combined organic phases are washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated by evaporation in vacuo
  9. customyielding 4.13 g (100% of the

Sources & evidence

ORD record
ord-152e94fc83414896bb30007e5c2cfe64
Source dataset
uspto-grants-1990_09
Patent number
US04957928

Reaction notes

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