Sodium Azide → 4H-Pyran-4-one, 2-(azidomethyl)-5-hydroxy-

HRID 1846829Notes

Reaction equation

HRID 1846829 reaction equation
Cl[CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.O>[N:11]([CH2:2][C:3]1[O:4][CH:5]=[C:6]([OH:10])[C:7](=[O:9])[CH:8]=1)=[N+:12]=[N-:13]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 82051Chlorokojic acid

Product 1

HCID 37033144H-Pyran-4-one, 2-(azidomethyl)-5-hydroxy-Yield 63.83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2-chloromethyl-5-hydroxy-pyran-4-one (2) (105.0 g, 656.2 mmol) in DMF (600 mL) was added NaN3 (55.45 g, 853.12 mmol) and the reaction mixture was stirred at room temperature for 16 h. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. Then, the combined organic layer was washed with water and brine, and dried over Na2SO4 and concentrated under reduced pressure to get 2-azidomethyl-5-hydroxy-pyran-4-one (3) (70.0 g, 63.83%) as a light brown solid.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. washThen, the combined organic layer was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-81f0c4cd7323465da561f644963da6d7
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

Loading…