Sodium Azide → 3-Azido-6-methoxyhexahydrofuro[3,2-b]furan

HRID 1053933Notes

Reaction equation

HRID 1053933 reaction equation
CS(O[CH:6]1[CH2:10][O:9][CH:8]2[CH:11]([O:14][CH3:15])[CH2:12][O:13][CH:7]12)(=O)=O.[N-:16]=[N+:17]=[N-:18].[Na+]>CN(C=O)C.C([O-])(O)=O.[Na+]>[N:16]([CH:6]1[CH2:10][O:9][CH:8]2[CH:11]([O:14][CH3:15])[CH2:12][O:13][CH:7]12)=[N+:17]=[N-:18]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 1183879396-Methoxyhexahydrofuro[3,2-b]furan-3-yl methanesulfonate

Product 1

HCID 1183879903-Azido-6-methoxyhexahydrofuro[3,2-b]furanYield 99.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 6-methoxyhexahydrofuro[3,2-b]furan-3-yl methanesulfonate (1.1 g, 4.6 mmol) in anhydrous DMF (25 mL) was added sodium azide (1.66 g, 25.5 mmol). The reaction was heated to 140° C. for 12 h and then diluted with NaHCO3 (sat, 50 mL), and extracted with EtOAc (80 mL×3). The organic layers were washed with H2O (30 mL×5), dried over Na2SO4, filtered and concentrated in vacuo to give the title compound as a light yellow solid (0.85 g, 99.4%).

Workup

  1. extractionextracted with EtOAc (80 mL×3)
  2. washThe organic layers were washed with H2O (30 mL×5)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b0e80a5d31d64bd7b56511a9792e995e
Source dataset
uspto-grants-2016_07
Patent number
US09394281B2

Reaction notes

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