Benzyl Bromide → 2-Azidomethyl-5-benzyloxy-pyran-4-one

HRID 1846830Notes

Reaction equation

HRID 1846830 reaction equation
[N:1]([CH2:4][C:5]1[O:6][CH:7]=[C:8]([OH:12])[C:9](=[O:11])[CH:10]=1)=[N+:2]=[N-:3].[OH-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[N:1]([CH2:4][C:5]1[O:6][CH:7]=[C:8]([O:12][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9](=[O:11])[CH:10]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 37033144H-Pyran-4-one, 2-(azidomethyl)-5-hydroxy-

Product 1

HCID 867256892-Azidomethyl-5-benzyloxy-pyran-4-oneYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 2-azidomethyl-5-hydroxy-pyran-4-one (3) (70.0 g, 419.1 mmol) in methanol (500 mL) was added NaOH (20 g, 502.9 mmol, 2M) and benzyl bromide (60.14 mL, 502.9 mmol) and the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, solvent was evaporated to remove volatile compounds under reduce pressure, then it was diluted with water and extracted with ethyl acetate. Then the combined organic layer was washed with water and brine, dried over Na2SO4, concentrated under reduced pressure and purified using normal column chromatography (using 20% ethyl acetate in hexane) to get 2-azidomethyl-5-benzyloxy-pyran-4-one (4) (60.0 g, 55.0%) as a light brown solid.

Workup

  1. customAfter completion of the reaction, solvent
  2. customwas evaporated
  3. customto remove volatile compounds
  4. additionit was diluted with water
  5. extractionextracted with ethyl acetate
  6. washThen the combined organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. custompurified

Sources & evidence

ORD record
ord-68622da431074d098e32e718e9bc4bef
Source dataset
uspto-grants-2015_02
Patent number
US08952039B2

Reaction notes

Loading…